Cyclic transition state in the acid catalyzed intramolecular allylstannane-aldehyde condensation

Vladimir Gevorgyan; Isao Kadota; Yoshinori Yamamoto

doi:10.1016/S0040-4039(00)91783-0

Cyclic transition state in the acid catalyzed intramolecular allylstannane-aldehyde condensation

Vladimir Gevorgyan, Isao Kadota, Yoshinori Yamamoto

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

61 Scopus citations

Abstract

Brφnsted acid catalyzed or Bu₄NF-TiCl₄ mediated cyclization of (Z)-ω-stannyl ether aldehyde 1a gives 2a, whereas (E)-isomer 1b affords 2b. To explain this stereochemical outcome, a push mechanism is proposed.

Original language	English (US)
Pages (from-to)	1313-1316
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4039(00)91783-0
State	Published - Feb 19 1993
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Cyclic transition state in the acid catalyzed intramolecular allylstannane-aldehyde condensation",

abstract = "Brφnsted acid catalyzed or Bu4NF-TiCl4 mediated cyclization of (Z)-ω-stannyl ether aldehyde 1a gives 2a, whereas (E)-isomer 1b affords 2b. To explain this stereochemical outcome, a push mechanism is proposed.",

author = "Vladimir Gevorgyan and Isao Kadota and Yoshinori Yamamoto",

year = "1993",

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doi = "10.1016/S0040-4039(00)91783-0",

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journal = "Tetrahedron Letters",

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T1 - Cyclic transition state in the acid catalyzed intramolecular allylstannane-aldehyde condensation

AU - Gevorgyan, Vladimir

AU - Kadota, Isao

AU - Yamamoto, Yoshinori

PY - 1993/2/19

Y1 - 1993/2/19

N2 - Brφnsted acid catalyzed or Bu4NF-TiCl4 mediated cyclization of (Z)-ω-stannyl ether aldehyde 1a gives 2a, whereas (E)-isomer 1b affords 2b. To explain this stereochemical outcome, a push mechanism is proposed.

AB - Brφnsted acid catalyzed or Bu4NF-TiCl4 mediated cyclization of (Z)-ω-stannyl ether aldehyde 1a gives 2a, whereas (E)-isomer 1b affords 2b. To explain this stereochemical outcome, a push mechanism is proposed.

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U2 - 10.1016/S0040-4039(00)91783-0

DO - 10.1016/S0040-4039(00)91783-0

M3 - Article

AN - SCOPUS:0027530713

SN - 0040-4039

VL - 34

SP - 1313

EP - 1316

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

Cyclic transition state in the acid catalyzed intramolecular allylstannane-aldehyde condensation

Abstract

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