Hydrogen-bond-mediated asymmetric cascade reaction of stable sulfur ylides with nitroolefins: scope, application and mechanism

Chemistry : a European Journal
Liang-Qiu LuWen-Jing Xiao

Abstract

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.

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Citations

Jan 31, 2015·Organic & Biomolecular Chemistry·Chunyin ZhuLong-Wu Ye
May 15, 2012·Accounts of Chemical Research·Liang-Qiu LuWen-Jing Xiao
Aug 6, 2013·Journal of the American Chemical Society·Yukihiro FukataSeijiro Matsubara
Apr 16, 2014·The Journal of Organic Chemistry·Amina BoucherifWen-Jing Xiao

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