Letter

pubs.acs.org/OrgLett

Divergent Access to Functionalized Pyrrolidines and Pyrrolines via

Iridium-Catalyzed Domino-Ring-Opening Cyclization of Vinyl
Aziridines with β‑Ketocarbonyls
Tao-Yan Lin, Hai-Hong Wu, Jian-Jun Feng,* and Junliang Zhang*
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China
Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China
*
S Supporting Information
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ABSTRACT: A useful synthesis of five-membered N-hetero-

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cycles has been developed through an iridium-catalyzed

domino-ring-opening cyclization of vinylaziridines with β-
ketocarbonyls. α-Substituted 1,3-dicarbonyls reacted with
vinylaziridines to give 2-methylenepyrrolidines bearing two
adjacent sp3-carbon centers with moderate to excellent
diastereoselectivity, while the reaction of α-unsubstituted 1,3-
dicarbonyls afforded 2-pyrrolines in good yield.

P yrrolidines and pyrrolines are abundant in many biologically

active natural products and pharmaceuticals (Figure 1).1
arylaziridines with active methylene compounds tends to
proceed selectively at the benzylic position,5,6 there would
appear to be only three previous reports involving the ring-
opening reactions of vinylaziridines with 1,3-dicarbonyls, but
providing the corresponding products via an SN2′ mechanism
(Scheme 1a).7 In 2010, Ghorai and co-workers reported their
pioneering work on the copper-catalyzed domino ring-opening

Scheme 1. Reactions between Vinylaziridines and 1,3-

Dicarbonyls

Figure 1. Pyrrolidines and pyrrolines structural motifs in biologically

active natural products and pharmaceuticals.

Therefore, the discovery of efficient synthetic methodologies to

access these compounds continues to attract the attention of
organic chemists, and numerous routes have been developed.2
However, the development of simple and efficient methods for
the syntheses of structurally diverse, polysubstituted, and
functionalized pyrrolidine and pyrroline derivatives is still in
great demand.
Aziridines, the smallest nitrogen-containing heterocycle, are
increasingly being exploited as building blocks for synthesis of
various N-heterocycles.3 Among these, nucleophilic ring-open-
ing cyclizations of aziridines with C-nucleophiles bearing both
nucleophilic and electrophilic moieties represent powerful tools
that permit efficient access to pyrrolidine and pyrroline
derivatives.4 Although many reports are known for the above
ring-opening cyclization reactions of aryl- or alkylaziridines, the
domino ring-opening cyclization involving vinylaziridines with Received: October 17, 2017
1,3-dicarbonyls is still limited.4a Moreover, while ring openings of Published: November 22, 2017

© 2017 American Chemical Society 6526 DOI: 10.1021/acs.orglett.7b03232

Org. Lett. 2017, 19, 6526−6529
Organic Letters
cyclization of aziridines with enolates for the synthesis of chiral γ-
lactams.4a Unfortunately, there was only one example involving a
vinylaziridine in Ghorai’s work and the corresponding γ-lactam
product was obtained from SN2-type ring-opening at the C-2
position of the vinylaziridine followed by cyclization. Moreover,
the SN2′ nucleophilic ring-opening product was also obtained as
a side product (Scheme 1b). To the best of our knowledge, there
is no report on the domino ring-opening at the C-3 position with
attendant cyclization of vinylaziridines with α-substituted 1,3-
dicarbonyls to provide products with quaternary centers. As a
part of our program of development of new reactions of
vinylaziridines to synthesize nitrogen-containing heterocycles,8
herein we report a convenient preparation of 2-methylenepyrro-
lidines bearing two adjacent stereocenters, one of which is a
quaternary carbon stereocenter and functionalized 2,3-dihydro-
pyroles through an iridium-catalyzed domino ring-opening
cyclizations of vinylaziridines with β-ketocarbonyls (Scheme
1c).8c,9
An initial scouting reaction was performed with vinylaziridine
1a and methylacetylacetone 2a in the presence of various
rhodium catalysts (see Table S1). After many attempts, we found
that the reaction afforded the desired 2-methylenepyrrolidine
3aa in 73% NMR yield with 7:1 dr when [Rh(NBD)Cl]2/
AgSbF6 was used as the catalyst. Next, other commonly used
transition-metal catalysts were tested. Compound 1a decom-
posed quickly under the catalysis of Pd(PPh3)47 and Cu(OTf)2.4a
Gratifyingly, treatment of 1a and 2a with [Ir(COD)Cl]2/AgSbF6
in DCE for 2 h at room temperature gave 3aa in 90% NMR yield
with 10:1 dr, while [Ir(COD)Cl]2 itself failed to catalyze this
reaction.
With optimal reaction conditions in hand, we set out to
investigate the scope of the current reaction with respect to the
vinylaziridine. As depicted in Scheme 2, the R2 group of
vinylaziridines 1 exhibited general tolerance. Both alkyl (1a−d)
Scheme 2. Preparation of 2-Methylenepyrrolidinesa
a proceeded smoothly, thus providing options for N-protection
Standard conditions: 1 (0.2 mmol), 2 (1.5 equiv), [Ir(COD)Cl]2 (5
mol %), AgSbF6 (10 mol %), DCE (2 mL), room temperature, 2 h.
Total isolated yield of two isomers and the dr value was determined by
H1 NMR of the crude product. bThe reaction was carried out under
the standard conditions for 2 h, and then DCE was removed under
vacuum followed by heating the crude product at reflux in CHCl3 for
12−18 h.
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Letter
and aryl (1e−h) groups could be readily incorporated, and the
reaction gave the corresponding 2-methylenepyrrolidines
bearing two adjacent stereocenters, one of which was a
quaternary carbon stereocenter, in moderate to good yield
with high to excellent diastereoselectivity. The structure and
relative stereochemistry of 3ha were confirmed by X-ray
crystallography. Of note, the substrate 1b possessing a CF3
group was found to be a suitable substrate, yielding the
corresponding product 3ba as a single diastereomer in 78%
yield. We next turned our attention to examining the generality of
1,3-diketones 2 in the presence of vinylaziridine 1a and the
iridium catalyst. Interestingly, compared to 1,3-diketone 2a,
substrates with an ethyl and an n-butyl group at the α-position
deliver the corresponding products 3′ab and 3′ac as the major
diastereomers, respectively (Scheme 3a). However, 3ab and 3ac
Scheme 3. Transformation from 3′ to 3
were obtained as the major diastereomers upon heating the crude
product in CHCl3 (Scheme 2). To test whether 3 arose from
isomerization of 3′, we subjected 3′ab and 3′ac in CHCl3 at
room temperature for 16 h in the absence of the Ir catalyst.
Compounds 3ab and 3ac were also obtained as the major
diastereomers (Scheme 3b,c). These results indicate that 3 is a
thermally more stable diastereomer. Besides alkyl groups (3aa−
ac), allyl (3ad) and ester groups (3ae and 3af) were compatible
with the standard conditions. Notably, the reaction gave the 2-
methylenepyrrolidine product 3af rather than the corresponding
γ-lactam when 2f was used as the substrate, which is quite
different from Ghorai’s work.4a Unsymmetric 1,3-diketone 2g
was examined in the reaction and showed good reactivity,
yielding 3ag as a single diastereomer. The reaction of 4-
methylheptane-3,5-dione 2h gave a slightly lower yield of 3ah
and diastereoselectivity than that with 2a. Besides acyclic 1,3-
dicarbonyls, cyclic 1,3-diketone 2i also worked in the current
reaction but showed low activity and diastereoselectivity.
To further extend the substrate scope, α-unsubstituted 1,3-
dicarbonyls 2 (R4 = H) were examined under the standard
conditions. However, a strikingly different reaction pattern was
observed when we applied α-unsubstituted 1,3-dicarbonyls as the
substrates. The reaction between 1a and 2j with [Ir(COD)Cl]2/
AgSbF6 in DCE for 2 h at room temperature proceeded smoothly
to furnish the 2,3-dihydropyrole 4aj rather than the correspond-
ing 2-methylenepyrrolidine product in 85% yield (Scheme 4).
The substrate scope was further investigated with respect to
variation of the vinylaziridine component. Varying the vinyl
moiety in 1 (bearing both alkyl and aryl subsitituents) was well
tolerated and produced 4aj−fj and 4hj in moderate to high yield.
The reactions of the N-tosyl 1i, N-nosyl 1j, and N-mesyl 1k
and deprotection of the corresponding pyrrolines. The scope
with regard to the β-ketocarbonyl component was also
investigated. Both symmetric (2j−k) and unsymmetric (2l−n)
1,3-diketones delivered the corresponding 2,3-dihydropyroles
(4aj−an) in 49−71% yield with excellent regioselectivity. We
also examined β-ketoester 2o as the nucleophile. The reaction
DOI: 10.1021/acs.orglett.7b03232
Org. Lett. 2017, 19, 6526−6529
Organic Letters
Scheme 4. Preparation of 2,3-Dihydropyrolesa
a
Standard conditions: 1 (0.2 mmol), 2 (1.5 equiv), [Ir(COD)Cl]2 (5
mol %), AgSbF6 (10 mol %), DCE (2 mL), room temperature, 2 h.
afforded 4ao rather than the corresponding γ-lactam in
acceptable yield.4a
The synthetic application of this methodology was demon-
strated in a number of transformations on the highly function-
alized 2-methylenepyrrolidine (Scheme 5). The isopropenyl
Scheme 5. Synthetic Transformations
group in 3aa could be selectively hydrogenated to produce the
corresponding 5aa in 89% yield. The oxidative cleavage of all
double bonds was realized by ozonolysis followed by reductive
workup, which give the γ-lactam 6aa bearing a quaternary all-
carbon stereocenter in good yield and excellent diastereose-
lectivity. In addition, reduction of the carbonyl group with
DIBAL-H afforded 7aa in 90% yield with 3:1 dr. Finally, 2,3-
dihydropyrole 8aa was obtained in high yield by treatment of 3aa
with TsOH−H2O.
To gain insight into the reaction mechanism, we examined the
reaction of (R)-1a (98% ee) with 2a catalyzed by rhodium and
iridium catalysts, respectively (Scheme 6a). The reaction
catalyzed by [Rh(NBD)Cl]2/AgSbF6 gave (+)-3aa in 80% ee.
In contrast, racemic 3aa was obtained when [Ir(COD)Cl]2/
AgSbF6 was used as the catalyst. Further control experiments
revealed that (R)-1a would undergo more rapid racemization in
the presence of iridium catalyst than the reaction catalyzed by
rhodium catalyst (Scheme 6b). Moreover, the treatment of 1a
and 2a with [Ir(COD)Cl]2/AgSbF6 in the presence of 4 Å
molecular sieves in DCE for 30 min provided the desired 9aa in
98% NMR yield (Scheme 6c).
On the basis of the above results, a plausible mechanism is
proposed for the current reaction (Scheme 7). Coordination of
vinylaziridine 1 to the iridium catalyst gives complex A, which
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Letter
Scheme 6. Chirality Transfer and Control Experiments
Scheme 7. Proposed Mechanism
undergoes oxidative addition to furnish the (η3-allyl)iridium(III)
species B. Regioselective nucleophilic attack on the allyl fragment
affords the alkylation product 9 and regenerates the catalyst.10,11
Then, intramolecular cyclization of 9 would afford hemiaminal C.
Finally, dehydration of C via path a provides 2-methylenepyrro-
lidine product 3 as the final product. Alternatively, the generation
of the 2-pyrroline 4 is most likely preferred when R4 = H (path
b).
In conclusion, the first iridium-catalyzed domino ring-opening
cyclizations of vinylaziridines with β-ketocarbonyls has been
achieved. Switchable syntheses of functionalized 2-methylene-
pyrrolidines and 2-pyrrolines were realized by substrate control.
The salient features of this reaction include high atom-economy,
mild conditions, general substrate scope, and easy further
transformations of the products. Further studies including
mechanism and asymmetric catalysis are ongoing in this
laboratory and will be reported in due course.
■
ASSOCIATED CONTENT
*
S Supporting Information
The Supporting Information is available free of charge via the
Internet at . Experimental procedures, 1H and 13C NMR spectra
and HPLC date for all new products (PDF) X-ray crystallo-
graphic data for (R)-3ha(CIF) The Supporting Information is
available free of charge on the ACS Publications website at DOI:
10.1021/acs.orglett.7b03232.
Experimental procedures, 1H and 13C NMR spectra, and
HPLC data for all new products and X-ray data for 3ha
(PDF)
Accession Codes
CCDC 1572755 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge via
www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_
request@ccdc.cam.ac.uk, or by contacting The Cambridge
Crystallographic Data Centre, 12 Union Road, Cambridge
CB2 1EZ, UK; fax: +44 1223 336033.
DOI: 10.1021/acs.orglett.7b03232
Org. Lett. 2017, 19, 6526−6529
Organic Letters
■ AUTHOR INFORMATION
Corresponding Authors
*E-mail: jjfeng@chem.ecnu.edu.cn.
*E-mail: jlzhang@chem.ecnu.edu.cn.
ORCID
Hai-Hong Wu: 0000-0001-6266-8290
Jian-Jun Feng: 0000-0002-6094-3268
Junliang Zhang: 0000-0002-4636-2846
Notes
The authors declare no competing financial interest.
■
ACKNOWLEDGMENTS
We are grateful to the National Natural Science Foundation of
China (21373088, 21425205, 21602062), 973 Program
(2015CB856600), and Innovative Research Team in University.
■
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Org. Lett. 2017, 19, 6526−6529