185

Davis chiral oxaziridine reagents

Chiral N-sulfonyloxaziridines employed for asymmetric hydroxylation, etc.

RSO2

O
N

Ar

e.g.

S
O O O

R1

Cl
Cl
N

RSO2

O
N

Ar

O M

R1

M
N

Ar

O
SO2R

RSO2

O
Ar

R1

N
O
R1

M
O M
R1

Ar

SO2R

Example 12

1. NaHMDS, THF, 78 oC

O

O
Ph

2. THF, 78 C
O

PhSO2

O
N

Ph

O
Ph

OH

3. camphor sulfonic acid, THF

85%, 90% de

186

Example 25
o

O
Ph

NaHMDS, THF, 78 C

61%, 95% ee

Ph
Cl
Cl
N

OH

S
O O O

References
Davis, F. A.; Vishwakarma, L. C.; Billmers, J. M.; Finn, J. J. Org. Chem. 1984, 49,
3241. Franklin A. Davis developed this methodology while teaching at Drexel University, now he is at Temple University.
2 Evans, D. A.; Morrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346.
3
Davis, F. A.; Billmers, J. M.; Gosciniak, D. J.; Towson, J. C.; Bach, R. D. J. Org.
Chem. 1986, 51, 4240.
4
Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703. (Review).
5 Davis, F. A.; Weismiller, M. C. J. Org. Chem. 1990, 55, 3715.
6 Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919934. (Review).
7
Davis, F. A.; Thimma Reddy, R.; Weismiller, M. C. J. Am. Chem. Soc. 1989, 111,
5964.
8
Davis, F. A.; Kumar, A.; Chen, B.-C. J. Org. Chem. 1991, 56, 1143.
9
Davis, F. A.; Reddy, R. T.; Han, W.; Carroll, P. J. J. Am. Chem. Soc. 1992, 114, 1428.
10 Tagami, K.; Nakazawa, N.; Sano, S.; Nagao, Y. Heterocycles 2000, 53, 771.
11 Takeda, K.; Sawada, Y.; Sumi, K. Org. Lett. 2002, 4, 1031.
12 Chen, B.-C.; Zhou, P.; Davis, F. A.; Ciganek, E. Org. React. 2003, 62, 1356. (Review).
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