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

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....

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Autores principales: Sun, Kehuan, Tao, Cheng, Long, Bohua, Zeng, Xiaobin, Wu, Zhengzhi, Zhang, Ronghua
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9072942/
https://www.ncbi.nlm.nih.gov/pubmed/35530808
http://dx.doi.org/10.1039/c9ra06827a
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author Sun, Kehuan
Tao, Cheng
Long, Bohua
Zeng, Xiaobin
Wu, Zhengzhi
Zhang, Ronghua
author_facet Sun, Kehuan
Tao, Cheng
Long, Bohua
Zeng, Xiaobin
Wu, Zhengzhi
Zhang, Ronghua
author_sort Sun, Kehuan
collection PubMed
description 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.
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spelling pubmed-90729422022-05-06 Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates Sun, Kehuan Tao, Cheng Long, Bohua Zeng, Xiaobin Wu, Zhengzhi Zhang, Ronghua RSC Adv Chemistry 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. The Royal Society of Chemistry 2019-10-08 /pmc/articles/PMC9072942/ /pubmed/35530808 http://dx.doi.org/10.1039/c9ra06827a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Sun, Kehuan
Tao, Cheng
Long, Bohua
Zeng, Xiaobin
Wu, Zhengzhi
Zhang, Ronghua
Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates
title Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates
title_full Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates
title_fullStr Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates
title_full_unstemmed Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates
title_short Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates
title_sort highly stereoselective gram scale synthesis of all the four diastereoisomers of boc-protected 4-methylproline carboxylates
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9072942/
https://www.ncbi.nlm.nih.gov/pubmed/35530808
http://dx.doi.org/10.1039/c9ra06827a
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