Issue 55, 2019

Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates

Abstract

A general and practical synthetic process for all the four diastereoisomers of Boc-protected 4-methylproline carboxylates has been developed with essentially complete stereoselectivity on the gram scale, which represents the most diastereoselective preparation of 4-methylproline derivatives to date. This synthesis features an Evans asymmetric alkylation to elegantly establish the challenging stereochemistry of the 4-methyl group, providing valuable insights for the diastereoselective preparation of 4-substituted prolines.

Graphical abstract: Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
28 Aug 2019
Accepted
29 Sep 2019
First published
08 Oct 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 32017-32020

Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates

K. Sun, C. Tao, B. Long, X. Zeng, Z. Wu and R. Zhang, RSC Adv., 2019, 9, 32017 DOI: 10.1039/C9RA06827A

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