Synthesis of 2-Substituted 2-Amino Ketones by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-Alkenols

Tomoya Miura, Takamasa Tanaka, Qiang Zhao, Scott G. Stewart, Masahiro Murakami

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A study on a rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with 2-alkenols is reported. The reaction is initiated by insertion of an α-imino carbene into the O-H linkage of alcohol, forming a 2-alkenoxy enamide intermediate. A thermal [3,3]-sigmatropic rearrangement follows to yield 2-substituted 2-amino ketone in a stereoselective manner. The successful application of this methodology to a formal synthesis of (-)-α-conhydrine is also described.

Original languageEnglish
Article numbere1600320
Number of pages8
JournalHelvetica Chimica Acta
Volume100
Issue number2
DOIs
Publication statusPublished - Feb 2017

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