Synthesis 2019; 51(22): 4183-4197
DOI: 10.1055/s-0039-1690185
paper
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective [2,3]-Sigmatropic Rearrangement of N-Allyl Ammonium Ylides

Aleksandra Murre
,
Kristin Erkman
,
Sandra Kaabel
,
Ivar Järving
,
Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia   Email: tonis.kanger@taltech.ee
› Author Affiliations
The authors thank the Estonian Ministry of Education and Research (grants No. IUT 19-32, IUT 19-9, and PUT 1468) and the Centre of Excellence in Molecular Cell Engineering (2014-2020.4.01.15-0013) for financial support.
Further Information

Publication History

Received: 03 May 2019

Accepted after revision: 02 August 2019

Publication Date:
28 August 2019 (eFirst)

Abstract

A rapid and diastereoselective method was developed for the [2,3]-sigmatropic rearrangement of N-allyl ammonium ylides, affording products in up to 95% isolated yields and up to 97:3 dr; most of the desired products were formed within 1 minute. For the asymmetric reaction, a chiral auxiliary was introduced to the starting compound, affording the rearrangement product with high diastereoselectivities.

Supporting Information

 
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