One-Carbon Homologation of N-Sulfonylaziridines to Allylic Amines Using Dimethylsulfonium Methylide

Abstract

[reaction: see text]. Regio- and stereodefined allylic N-sulfonylamines are synthesized in high yields and under experimentally straightforward conditions by reaction of N-sulfonylaziridines with excess dimethylsulfonium methylide.

Directed addition of sulfur-stabilised carbanions to 1,2,3-trisubstituted aziridines

“…Aryl groups have been reported to show analogous directing effects, in ring-opening reactions of electron-rich arenes with arylaziridines involving S E Artype mechanisms. 4e9 The same regioselectivity has been reported for sulfur ylides 10,11 and organometallic reagents. 12 In contrast, reaction of vinylaziridines with organomagnesium 13 and organocopper 14e16 reagents frequently gives predominantly the products of S N 2 0 -type ring-opening.…”

Diastereoselective Nucleophilic Ring‐Opening Reactions of 2,6‐Diazasemibullvalenes for the Synthesis of Diverse Functionalized Δ1‐Bipyrroline Derivatives

“…Because we have an interest in the construction of novel bowl‐ or cage‐shaped compounds by reactions of NSBVs,3 we were curious whether ring expansion of the aziridine core in 1 with sulfoxonium ylides could generate new bowl‐shaped polycyclic frameworks that contained a strained four‐membered azetidine ring. However, to our surprise, when 1 a was treated with dimethylsulfoxonium ylide (4 equiv) in DMSO at 85 °C for 8 h, methylidene Δ 1 ‐bipyrroline 19 was isolated in 72 % isolated yield as sole product instead of the expected ring‐expansion product 20 21. The methylene CH 2 group unambiguously showed two singlets at δ =5.54 and 5.76 ppm in the 1 H NMR spectrum in CDCl 3 , which is in good accordance with structure 19 .…”

A Novel Approach Towards Dibenzylbutyrolactone Lignans Involving Heck and Radical Reactions: Application to (±)‐Matairesinol Synthesis

“…In the modified procedure, the ylide was generated using 3 equiv. of Me 3 SI and nBuLi [27] in THF, and the yield of the reaction improved to 80 %.…”