Gold-Catalyzed Synthesis of 3-Pyrrolidinones and Nitrones from N-Sulfonyl Hydroxylamines via Oxygen-Transfer Redox and 1,3-Sulfonyl Migration

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초록

Golden touch: Gold-catalyzed reaction of N-sulfonyl hydroxylamines with terminal alkyne led to 3-pyrrolidinones by means of an oygen-transfer redox reaction. This protocol constitutes a direct method for forming α-amino carbonyl compounds. In sharp contrast, those with internal alkynes underwent 1,3-sulfonyl migration leading to 3-sulfonyl cyclic nitrones.

키워드

goldhomogeneous catalysishydroxylaminesnitronespyrrolidinonesredox chemistryC-H BONDONE-POT SYNTHESISALKYNYL ETHERSACIDCYCLIZATION6-SULFONYLINDOLESHYDROALKYLATIONISOMERIZATIONREARRANGEMENTREACTIVITY
제목
Gold-Catalyzed Synthesis of 3-Pyrrolidinones and Nitrones from N-Sulfonyl Hydroxylamines via Oxygen-Transfer Redox and 1,3-Sulfonyl Migration
저자
Yeom, Hyun-SukSo, EunsuShin, Seunghoon
DOI
10.1002/chem.201002863
발행일
2011-12
유형
Article
저널명
Chemistry - A European Journal
17
6
페이지
1764 ~ 1767