Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates. Issue 55 (8th October 2019)

• Record Type: Journal Article
• Authors: Sun, Kehuan; Tao, Cheng; Long, Bohua; Zeng, Xiaobin; Wu, Zhengzhi; Zhang, Ronghua
• Is Part Of: RSC advances. Volume 9:Issue 55(2019)
• Page Start: 32017
• Page End: 32020
• Publication Date: 2019-10-08
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9ra06827a
• Languages: English
• ISSNs: 2046-2069

Abstract

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 gram scale. 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.