Highly diastereoselective desymmetrizing intramolecular cyclization of allylstannane with a diketone promoted by Lewis acid or transition metal complex

Takashi Shimada; Naoki Asao; Yoshinori Yamamoto

doi:10.1016/S0022-328X(00)00897-4

Highly diastereoselective desymmetrizing intramolecular cyclization of allylstannane with a diketone promoted by Lewis acid or transition metal complex

Takashi Shimada, Naoki Asao, Yoshinori Yamamoto

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

4 Citations (Scopus)

Abstract

The Lewis acid mediated de symmetrizing intramolecular cyclization of prochiral allylstannyl diketone (1) gave a mixture of two diastereomers (2 and 3). Highly diastereoselective synthesis of each of the diastereomers was accomplished by appropriate choice of the Lewis acid. Compound 3 was also produced stereoselectively by using a palladium catalyst instead of Lewis acid.

Original language	English
Pages (from-to)	136-142
Number of pages	7
Journal	Journal of Organometallic Chemistry
Volume	624
Issue number	1-2
DOIs	https://doi.org/10.1016/S0022-328X(00)00897-4
Publication status	Published - 2001 Apr 1

Keywords

Allylstannane
Desymmetrizing cyclization
Diketone
Lewis acid
Transition metal catalyst

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0022-328X(00)00897-4

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AU - Shimada, Takashi

AU - Asao, Naoki

AU - Yamamoto, Yoshinori

PY - 2001/4/1

Y1 - 2001/4/1

N2 - The Lewis acid mediated de symmetrizing intramolecular cyclization of prochiral allylstannyl diketone (1) gave a mixture of two diastereomers (2 and 3). Highly diastereoselective synthesis of each of the diastereomers was accomplished by appropriate choice of the Lewis acid. Compound 3 was also produced stereoselectively by using a palladium catalyst instead of Lewis acid.

AB - The Lewis acid mediated de symmetrizing intramolecular cyclization of prochiral allylstannyl diketone (1) gave a mixture of two diastereomers (2 and 3). Highly diastereoselective synthesis of each of the diastereomers was accomplished by appropriate choice of the Lewis acid. Compound 3 was also produced stereoselectively by using a palladium catalyst instead of Lewis acid.

KW - Allylstannane

KW - Desymmetrizing cyclization

KW - Diketone

KW - Lewis acid

KW - Transition metal catalyst

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ER -

Highly diastereoselective desymmetrizing intramolecular cyclization of allylstannane with a diketone promoted by Lewis acid or transition metal complex

Abstract

Keywords

ASJC Scopus subject areas

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