Synlett 2004(11): 1925-1928  
DOI: 10.1055/s-2004-830854
LETTER
© Georg Thieme Verlag Stuttgart · New York

Aza-Wittig Rearrangement of N,N-Dipropargylic α-Amino Alkyllithiums: Periselectivity and Steric Course

Takahiro Tomoyasu, Katsuhiko Tomooka*
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, Japan
Fax: +81(3)57343931; e-Mail: ktomooka@apc.titech.ac.jp;
Further Information

Publication History

Received 15 May 2004
Publication Date:
28 July 2004 (online)

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Abstract

The aza-Wittig rearrangement of enantio-defined N,N-dipropargylic α-amino alkyllithiums, generated by tin-lithium ­exchange, are shown to afford [1,2]- and/or [2,3]-rearrangement products. Both aza-Wittig rearrangements proceed predominantly with inversion of configuration at the Li-bearing carbon terminus.