Premium
Hydrogen‐Bond‐Mediated Asymmetric Cascade Reaction of Stable Sulfur Ylides with Nitroolefins: Scope, Application and Mechanism
Author(s) -
Lu LiangQiu,
Li Fang,
An Jing,
Cheng Ying,
Chen JiaRong,
Xiao WenJing
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201104021
Subject(s) - cascade , sulfur , annulation , chemistry , mechanism (biology) , scope (computer science) , combinatorial chemistry , hydrogen bond , molecule , computational chemistry , reaction mechanism , organic chemistry , catalysis , stereochemistry , computer science , physics , chromatography , quantum mechanics , programming language
A hydrogen‐bond‐mediated asymmetric [4+1] annulation/rearrangement cascade of stable sulfur ylides and nitroolefins was developed. This reaction provides a facile route to enantioenriched 4,5‐substituted oxazolidinones in moderate to excellent isolated yields (65–96 %) with excellent stereocontrol (up to more than 95:5 d.r. and 97:3 e.r.). This methodology was successfully applied to the concise synthesis of two bioactive molecules. The stereocontrolled modes and mechanism have been proposed to explain the origin of this stereochemistry.