An umpolung reaction of α-iminothioesters possessing a cyclopropyl group. Issue 17 (10th March 2020)

• Record Type: Journal Article
• Authors: Shimizu, Makoto; Morimoto, Takayoshi; Yanagi, Yusuke; Mizota, Isao; Zhu, Yusong
• Is Part Of: RSC advances. Volume 10:Issue 17(2020)
• Page Start: 9955
• Page End: 9963
• Publication Date: 2020-03-10
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0ra01152e
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Tandem N -alkylation/oxidation/second addition reaction to α-cyclopropyl α-imino(thio)esters gave N -alkylated ring-opened products in good yields. 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.