Cyclopropanation of Propargyl Sulfonium Salts: Highly Diastereoselective Synthesis of Alkynylcyclopropanes

Abstract

The first propargyl sulfur ylides involving a cyclopropanation reaction between propargyl sulfonium salts and acrylonitrile derivatives is presented. Propargyl sulfonium salts act as unusual alkyne-group-delivering reagents in this transformation. Various alkynylcyclopropanes bearing three contiguous stereocenters were constructed in moderate to high yields with excellent diastereoselectivity under mild reaction conditions.

Solvent-involved synthesis of pyrrolidin-5-one-2-carboxamides via a sequential Ugi/olefination reaction

“…1a). 4 The research groups of Aggarwal, 5 Tang, 6 Xiao, 7 Huang 8 and others 9 have disclosed many elegant reactions of sulfur ylides used to generate novel compounds. This traditional reactivity pattern utilizes sulfur ylides as intermediates to form various cyclic molecules through cycloaddition reactions.…”

Highly efficient construction of 2,3-disubstituted indoline derivatives by [4 + 1] annulation of sulfur ylides and o-sulfonamido aldimines

“…Since the pioneering work developed by Johnson, Corey and Chaykovsky in the 1960s, namely the Johnson–Corey–Chaykovsky reaction, 7 sulfur ylides could now be used as C1, C2, and C3 synthons in various cascade annulation reactions, providing many strategies to synthesize structurally diverse carbo- and hetero-cyclic compounds. 8 The research groups of Aggarwal, 9 Tang, 10 Xiao, 11 Huang 12 and others 13 have disclosed many elegant reactions of sulfur ylides used to generate novel compounds. As part of our ongoing research program on methods to synthesize carbo- and hetero-cycles, 14 we report an efficient synthesis of 2,3-disubstituted indolines that relies on metal-free [4 + 1] cycloaddition of sulfur ylides and o -sulfonamido aldimine (Fig.…”