
TY  - JOUR
A1  - Pyne, Stephen G. 
A1  - Schafer, Karl 
A1  - Skelton, Brian W. 
A1  - White, Allan H. 
T1  - Asymmetric Synthesis of Protected 2-Substituted Cyclopropane Amino Acids
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1998
VL  - 51
IS  - 2
SP  - 127
EP  - 136
KW  - 
UR  - https://doi.org/10.1071/C97105 
N2  - The cyclopropanation reactions of (1a) with ethyl and t-butyl (dimethylsulfuranylidene)acetate proceeded with good diastereoselectivity and resulted in the formation of three diastereoisomeric products. The major diastereoisomeric product ((2a) and (2b), respectively) could be isolated in pure form by simple recrystallization. The stereochemistry of the major cyclopropane product (2b) has been determined by single-crystal X-ray structural analysis. These cyclopropanation products were susceptible to ring opening of the cyclopropane ring upon reduction with sodium borohydride or acid hydrolysis. The reaction of (1b) with ethyl (dimethylsulfuranylidene)acetate gave a mixture of four diastereoisomeric cyclopropanation products. The reactions of (1a) and (1b) with the sulfur ylide derived from 3-methoxycarbonylallyldimethylsulfonium bromide were less successful in terms of product diastereoselectivities. 
ER  -

