Fukuyama Group - Group Meeting Problems

12/12/2012
1
1) N

CO2Me

Rh(OAc)4, CH2Cl2, rt, 60%

2) NBS, H2O/dioxane, rt, 66%
3) K2CO3, MeOH, rt, 94%

OBn

4) Et3SiH, TFA
CH2Cl2, 0 C to rt
92%

O
O

5) H2, Pd/C
MeOH, rt, 97%

OH

R. S. Perali et al., Tetrahedron, 68, 3725 (2012)

2
Ph

O
N
Me

OCOt-Bu
SMe
SMe

1) MeS-SMe2BF4
MeCN, 40 C;
Et3N
64%
2) benzene
reflux
61%

Me
N

SMe

O
O

Ph

A. Padwa et al., Heterocycles, 58, 227 (2002)

3
1) NaOH
H2O2
THF-H2O, rt
81% (2 steps)

Li

Ph

Et2O, 78 C;
W(CO)6

C29H41BO

BCl

CHO

BF3OEt2
CH2Cl2
15 C

2) PPTS
CH2(OMe)2
rt

Ph

90%

Et2O
78 C to rt

J. Barluenga et al., Org. Lett., 5, 905 (2003)

1) 2-Bromoethanol
EtOH, 80%

3) BrCN, NaHCO3
MeOH, 0 C, 50%

2) Ethyl vinyl ether

CaCO3, H2O, rt
90%

4) BnBr, MeCN; evap.;

NaBH4, MeOH, rt
50%

EtO
OMe
BnN

NC

Y. Langlois et al., Tetrahedron Lett., 36, 9475 (1995)

Fukuyama Group - Group Meeting Problems

12/19/2012
1

DMSO
HCl (gas)
C15H14N2

AcOH
rt

NH2

Ac2O

DMDO (1 eq)

53%

acetone
rt

acetone
rt

quant

77%

N
N

X. Qian et al., Synthesis, 8, 1228 (2005)

M. Harmata et al., Eur. J. Org. Chem., 7053 (2012)

chloroacetonitrile (2.5 eq.)

AlCl3 (1.2 eq.)
BCl3 (1.2 eq.)

AllylMgBr (2.5 eq.)

CH2Cl2
0 C to reflux

THF
10 C to rt

64%

89%

NH2
Cl

Cl

N
H

Tao Pei et al., Tetrahedron, 65, 3285 (2009)

1)
OMe

OH

p-TsOH (cat.)
toluene, reflux
77%

MeO

HO

NHCO2Me

OMOM

2) LiAlH4
THF, reflux
95%

OMe
MeO

3) PhSO2Cl, Et3N
CH2Cl2, 0 C to rt
82%
4) Li, NH3
t-BuOH-THF, 78 C
76%

NMe
H

O
O

K. Ogasawara et al., Org. Lett., 4, 4515 (2002)

4
O

Cl

1) n-BuLi (5 eq)
THF, 35 C
95%

H
O

C15H24O2
2) NaBH3CN
BF3OEt2
CH2Cl2, rt, 74%
3) DMP, H2O
CH2Cl2, 0 C to rt
86%

1) TESOTf
Et3N
CH2Cl2, rt
TESO
95%
2) catalyst
CH2Cl2, rt
65%

Ar N
O
H

N Ar

SbF6
Au
NCPh
Ar=2,6-(i-Pr)2C6H3
catalyst

A. M. Echavarren et al., Chem. Commun., 7327 (2009)