α,β-epoxy vinyl triflates in Pd-catalyzed reactions

Kana Yamamoto; Clayton H. Heathcock

doi:10.1021/ol000064e

α,β-epoxy vinyl triflates in Pd-catalyzed reactions

Kana Yamamoto, Clayton H. Heathcock^*

^*Corresponding author for this work

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

20 Citations (Scopus)

Abstract

(matrix presented) Reactions of steroidal αβ-epoxy vinyl triflates in Pd-catalyzed reactions are described. Oxidative insertion of Pd⁰ into the C-O bond, giving vinylpalladium 12, is faster than formation of the π-allyl derivative from the vinyl epoxide. Although 12 can be trapped under certain conditions, it eventually rearranges to palladium alkoxide 14, which is in equilibrium with 15 and/or 10.

Original language	English
Pages (from-to)	1709-1712
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	12
DOIs	https://doi.org/10.1021/ol000064e
Publication status	Published - 2000 Jun 15
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol000064e

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title = "α,β-epoxy vinyl triflates in Pd-catalyzed reactions",

abstract = "(matrix presented) Reactions of steroidal αβ-epoxy vinyl triflates in Pd-catalyzed reactions are described. Oxidative insertion of Pd0 into the C-O bond, giving vinylpalladium 12, is faster than formation of the π-allyl derivative from the vinyl epoxide. Although 12 can be trapped under certain conditions, it eventually rearranges to palladium alkoxide 14, which is in equilibrium with 15 and/or 10.",

author = "Kana Yamamoto and Heathcock, {Clayton H.}",

year = "2000",

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doi = "10.1021/ol000064e",

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T1 - α,β-epoxy vinyl triflates in Pd-catalyzed reactions

AU - Yamamoto, Kana

AU - Heathcock, Clayton H.

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N2 - (matrix presented) Reactions of steroidal αβ-epoxy vinyl triflates in Pd-catalyzed reactions are described. Oxidative insertion of Pd0 into the C-O bond, giving vinylpalladium 12, is faster than formation of the π-allyl derivative from the vinyl epoxide. Although 12 can be trapped under certain conditions, it eventually rearranges to palladium alkoxide 14, which is in equilibrium with 15 and/or 10.

AB - (matrix presented) Reactions of steroidal αβ-epoxy vinyl triflates in Pd-catalyzed reactions are described. Oxidative insertion of Pd0 into the C-O bond, giving vinylpalladium 12, is faster than formation of the π-allyl derivative from the vinyl epoxide. Although 12 can be trapped under certain conditions, it eventually rearranges to palladium alkoxide 14, which is in equilibrium with 15 and/or 10.

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α,β-epoxy vinyl triflates in Pd-catalyzed reactions

Abstract

ASJC Scopus subject areas

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