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

doi:10.1016/S0040-4020(01)85543-5

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 journal › Article › peer-review

1 Citation (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 language	English
Pages (from-to)	9775-9780
Number of pages	6
Journal	Tetrahedron
Volume	50
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4020(01)85543-5
Publication status	Published - 1994
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

author = "Takatoshi Matsumoto and Toyohiko Aoyama and Takayuki Shioiri and Eiji Osawa",

year = "1994",

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AU - Matsumoto, Takatoshi

AU - Aoyama, Toyohiko

AU - Shioiri, Takayuki

AU - Osawa, Eiji

PY - 1994

Y1 - 1994

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AB - 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.

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JF - Tetrahedron

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ER -

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

Abstract

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