Stereoselective ring expansion of vinyl oxiranes: Mechanistic insights and natural product total synthesis

Matthew Brichacek; Lindsay A. Batory; Jon T. Njardarson

doi:10.1002/anie.200906830

Stereoselective ring expansion of vinyl oxiranes: Mechanistic insights and natural product total synthesis

Matthew Brichacek, Lindsay A. Batory, Jon T. Njardarson

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

47 Scopus citations

Abstract

"Chemical Equation Presented" What a (strain) relief! The first broadly applicable, catalytic, and stereoselective vinyl oxirane ring expansion is described (see scheme; hfacac = hexafluoroacetylacetonate). The stereoselectivity was influenced by several reaction parameters, and kinetic studies support a mechanistic proposal involving the in situ formation of a more reactive catalytic species. This ring-expansion reaction has been employed in the asymmetric total synthesis of (+)-goniothalesdiol.

Original language	English (US)
Pages (from-to)	1648-1651
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	9
DOIs	https://doi.org/10.1002/anie.200906830
State	Published - Feb 22 2010
Externally published	Yes

Keywords

Copper
Natural products
Oxiranes
Stereoselectivity
Total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200906830

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keywords = "Copper, Natural products, Oxiranes, Stereoselectivity, Total synthesis",

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AU - Batory, Lindsay A.

AU - Njardarson, Jon T.

PY - 2010/2/22

Y1 - 2010/2/22

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AB - "Chemical Equation Presented" What a (strain) relief! The first broadly applicable, catalytic, and stereoselective vinyl oxirane ring expansion is described (see scheme; hfacac = hexafluoroacetylacetonate). The stereoselectivity was influenced by several reaction parameters, and kinetic studies support a mechanistic proposal involving the in situ formation of a more reactive catalytic species. This ring-expansion reaction has been employed in the asymmetric total synthesis of (+)-goniothalesdiol.

KW - Copper

KW - Natural products

KW - Oxiranes

KW - Stereoselectivity

KW - Total synthesis

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Stereoselective ring expansion of vinyl oxiranes: Mechanistic insights and natural product total synthesis

Abstract

Keywords

ASJC Scopus subject areas

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