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An umpolung reaction of α-iminothioesters possessing a cyclopropyl group†
Takayoshi Morimoto,Yusuke Yanagi,Isao Mizota,Yusong Zhu
RSC Advances Pub Date : 03/10/2020 00:00:00 , DOI:10.1039/D0RA01152E
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
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