An efficient stereoselective synthesis of .DELTA.4,5-pipecolic esters
摘要:
The synthesis of racemic and enantiomerically homogeneous pipecolic esters from 1-amino-3-buten-2-ols is reported. The synthesis of enantiomerically homogeneous N-methylpipecolic esters requires four chemical steps from N-t-BOC-protected amino esters. The key step of the sequence is a conformationally restricted Claisen rearrangement. The method affords complete control of the absolute and relative stereochemistry of all three stereogenic centers in pipecolic ester 22 which is obtained in 33% overall yield from N-t-BOC-L-alanine ethyl ester 16a.
An efficient stereoselective synthesis of .DELTA.4,5-pipecolic esters
作者:Steven R. Angle、J. Guy Breitenbucher、Damian O. Arnaiz
DOI:10.1021/jo00048a030
日期:1992.10
The synthesis of racemic and enantiomerically homogeneous pipecolic esters from 1-amino-3-buten-2-ols is reported. The synthesis of enantiomerically homogeneous N-methylpipecolic esters requires four chemical steps from N-t-BOC-protected amino esters. The key step of the sequence is a conformationally restricted Claisen rearrangement. The method affords complete control of the absolute and relative stereochemistry of all three stereogenic centers in pipecolic ester 22 which is obtained in 33% overall yield from N-t-BOC-L-alanine ethyl ester 16a.