Issue 17, 2020

An umpolung reaction of α-iminothioesters possessing a cyclopropyl group

Abstract

An umpolung N-alkylation reaction of α-cyclopropyl α-iminothioesters with diethylaluminum chloride or ethylmagnesium bromide affords the corresponding N-ethylated α-aminothioesters in good yields. Subsequent oxidation and reaction of the N-ethylated product with a thiolate or a chloride anion proceed effectively to give the ring-opened products in good yields. In contrast, relatively “hard” nucleophiles did not give the ring-opened products but gave the addition products to the iminium carbon.

Graphical abstract: An umpolung reaction of α-iminothioesters possessing a cyclopropyl group

Supplementary files

Article information

Article type
Paper
Submitted
06 Febr. 2020
Accepted
03 Marts 2020
First published
10 Marts 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 9955-9963

An umpolung reaction of α-iminothioesters possessing a cyclopropyl group

M. Shimizu, T. Morimoto, Y. Yanagi, I. Mizota and Y. Zhu, RSC Adv., 2020, 10, 9955 DOI: 10.1039/D0RA01152E

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