Tetrahedron

Novel stereocontrolled approach to conformationally constrained analogues of l-glutamic acid and l-proline via stereoselective cyclopropanation of 3, 4-didehydro-l- …

M Oba, N Nishiyama, K Nishiyama

Index: Oba, Makoto; Nishiyama, Naohiro; Nishiyama, Kozaburo Tetrahedron, 2005 , vol. 61, # 35 p. 8456 - 8464

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Citation Number: 29

Abstract

A new stereocontrolled approach to l-(carboxycyclopropyl) glycines (l-CCGs) and 3, 4- methano-l-prolines, conformationally constrained analogues of l-glutamic acid and l-proline, respectively, was developed using a 3, 4-didehydro-l-pyroglutamate derivative as a common chiral template. The unsaturated l-pyroglutamate derivative employed in this work is a novel chiral synthon in which the carboxyl functionality is protected as a 2, 7, 8-trioxabicyclo [3.2. ...