Synlett 2012; 23(15): 2266-2268
DOI: 10.1055/s-0031-1290458
letter
© Georg Thieme Verlag Stuttgart · New York

Allylation Reactions of N,O-Heterocycles

Roderick W. Bates*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore, Singapore, Fax: +6567911961   Email: roderick@ntu.edu.sg
,
Chi H. Tang
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore, Singapore, Fax: +6567911961   Email: roderick@ntu.edu.sg
,
Yuting Tan
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore, Singapore, Fax: +6567911961   Email: roderick@ntu.edu.sg
,
Siti Nurhayati binte Buang
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore, Singapore, Fax: +6567911961   Email: roderick@ntu.edu.sg
› Author Affiliations
Further Information

Publication History

Received: 31 May 2012

Accepted after revision: 01 July 2012

Publication Date:
17 August 2012 (online)


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Abstract

Iminium ions generated from isoxazolidines and tetrahydro-1,2-oxazines undergo allylation under Sakurai conditions. Allylated isoxazolidines are formed predominantly as the trans isomer, while oxazines are formed exclusively as the cis isomer.