Modified cyclization of enantio-enriched α-homoallyloxyalkyllithiums generated by Sn-Li transmetallation: Effects of additives and structural requirement

Nobuyuki Komine; Katsuhiko Tomooka; Takeshi Nakai

doi:10.3987/com-99-s135

Modified cyclization of enantio-enriched α-homoallyloxyalkyllithiums generated by Sn-Li transmetallation: Effects of additives and structural requirement

Nobuyuki Komine, Katsuhiko Tomooka, Takeshi Nakai

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

The titled cyclization, when performed in the presence of lithium chloride, afforded an improved yield of the enantio-enriched 2,3-trans- disubstituted tetrahydrofuran derivative in high diastereoselectivity, whereas a similar cyclization in the presence of zinc bromide gave the 2,3- cis isomer as the major product in lower enantiopurity.

Original language	English
Pages (from-to)	1071-1074
Number of pages	4
Journal	Heterocycles
Volume	52
Issue number	3
DOIs	https://doi.org/10.3987/com-99-s135
Publication status	Published - Mar 1 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "The titled cyclization, when performed in the presence of lithium chloride, afforded an improved yield of the enantio-enriched 2,3-trans- disubstituted tetrahydrofuran derivative in high diastereoselectivity, whereas a similar cyclization in the presence of zinc bromide gave the 2,3- cis isomer as the major product in lower enantiopurity.",

author = "Nobuyuki Komine and Katsuhiko Tomooka and Takeshi Nakai",

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AU - Tomooka, Katsuhiko

AU - Nakai, Takeshi

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N2 - The titled cyclization, when performed in the presence of lithium chloride, afforded an improved yield of the enantio-enriched 2,3-trans- disubstituted tetrahydrofuran derivative in high diastereoselectivity, whereas a similar cyclization in the presence of zinc bromide gave the 2,3- cis isomer as the major product in lower enantiopurity.

AB - The titled cyclization, when performed in the presence of lithium chloride, afforded an improved yield of the enantio-enriched 2,3-trans- disubstituted tetrahydrofuran derivative in high diastereoselectivity, whereas a similar cyclization in the presence of zinc bromide gave the 2,3- cis isomer as the major product in lower enantiopurity.

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Modified cyclization of enantio-enriched α-homoallyloxyalkyllithiums generated by Sn-Li transmetallation: Effects of additives and structural requirement

Abstract

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