Effect of zinc halides on the high stereoselectivity of a new mannich type cyclization in the tilivalline synthesis a computational chemical analysis

Takatoshi Matsumoto, Toyohiko Aoyama, Takayuki Shioiri, Eiji Osawa

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The calculation by the semi-empirical molecular orbital method concerning the effect of zinc halides on the high stereoselectivity of a new Mannich type cyclization in our tilivalline synthesis has revealed that (1) zinc chloride coordinates with the N10 atom during the reaction and (2) the steric hindrance on the α side and the extension of LUMO to the β side in the intermediate 7 govern the high steroselectivity.

Original languageEnglish
Pages (from-to)9775-9780
Number of pages6
JournalTetrahedron
Volume50
Issue number32
DOIs
Publication statusPublished - 1994
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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