Stereo- and Regioselective Formation of Silyl-Dienyl Boronates

Lauren Kaminsky; Robert J. Wilson; Daniel A. Clark

doi:10.1021/acs.orglett.5b01434

Stereo- and Regioselective Formation of Silyl-Dienyl Boronates

Lauren Kaminsky, Robert J. Wilson, Daniel A. Clark

Department of Chemistry

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

10 Scopus citations

Abstract

The intramolecular trans-silylruthenation of internal alkynes and subsequent insertion of vinyl boronates is described. This approach provides complete regiocontrol through a stereoselective trans-5-exo-dig cyclization which affords a tetrasubstituted olefin as a vinylsilane and a highly functionalized Z,E diene motif.

Original language	English (US)
Pages (from-to)	3126-3129
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.5b01434
State	Published - Jun 19 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5b01434

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title = "Stereo- and Regioselective Formation of Silyl-Dienyl Boronates",

abstract = "The intramolecular trans-silylruthenation of internal alkynes and subsequent insertion of vinyl boronates is described. This approach provides complete regiocontrol through a stereoselective trans-5-exo-dig cyclization which affords a tetrasubstituted olefin as a vinylsilane and a highly functionalized Z,E diene motif.",

author = "Lauren Kaminsky and Wilson, {Robert J.} and Clark, {Daniel A.}",

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AU - Kaminsky, Lauren

AU - Wilson, Robert J.

AU - Clark, Daniel A.

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Y1 - 2015/6/19

N2 - The intramolecular trans-silylruthenation of internal alkynes and subsequent insertion of vinyl boronates is described. This approach provides complete regiocontrol through a stereoselective trans-5-exo-dig cyclization which affords a tetrasubstituted olefin as a vinylsilane and a highly functionalized Z,E diene motif.

AB - The intramolecular trans-silylruthenation of internal alkynes and subsequent insertion of vinyl boronates is described. This approach provides complete regiocontrol through a stereoselective trans-5-exo-dig cyclization which affords a tetrasubstituted olefin as a vinylsilane and a highly functionalized Z,E diene motif.

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JO - Organic Letters

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Stereo- and Regioselective Formation of Silyl-Dienyl Boronates

Abstract

ASJC Scopus subject areas

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