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Updated: Jun 3, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Stereoselectivity in nucleophilic additions to 3-azidoalkanals
Chan Woo Huh1, Chad Schroeder, Gurpreet Singh
1The University of Kansas Chemical Methodologies and Library Development Center, 2034 Becker Dr., Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, USA.
Abstract:
The stereoselectivity of nucleophilic additions to 3-azidoalkanals was investigated. Non-chelating, BF(3)·OEt(2)-mediated Sakurai addition to 3-azidoalkanals afforded 1,3-anti products, whereas use of a chelating Lewis acid, TiCl(4), resulted in 1,3-syn products with moderate selectivity. A boat-like chelation structure of the 3-azidoalkanal with the Lewis acid is proposed to be consistent with the 1,3-syn selectivity of the reactions. Mukaiyama aldol addition to 3-azidohexanal generated 1,3-anti products regardless of the chelating ability of the Lewis acid.
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