Zinc-mediated allylation and alkylation of aminals in the presence of TMSCl and diisopropylamine

  • J Org Chem. 2008 Nov 21;73(22):9188-91. doi: 10.1021/jo8019797.
Bunpei Hatano  1 ,  Keita Nagahashi ,  Tatsuro Kijima
Affiliations
  • 1. Division of Chemistry, Graduate School of Science and Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa, 992-8510, Japan. [email protected]
PMID: 18947253 DOI: 10.1021/jo8019797
Abstract

An alkylation of aminals with organozinc reagents derived from allyl bromide, benzyl bromide, alpha-bromoacetate, and alpha-bromonitrile proceeded efficiently in the presence of TMSCl and diisopropylamine. This reaction system was applied to the synthesis of an antispasmodic: butaverine.

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