The Catalytic Addition of Alkyl Boranes to Alkynyl Esters Affording Single-Isomer Trisubstituted Olefins

The generation of a series of trisubstituted olefins bearing alkyl substituents is described using a stereoselective and regioselective addition to alkynyl esters. The method produces trisubstituted olefins as single isomers using a convenient and mild transformation in which alkyl boranes are cross...

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Bibliographic Details
Published inSynlett no. 8; pp. 1113 - 1116
Main Authors Rajagopal, Thivisha, Ogilvie, William W.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.05.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
regioselectivity
CARBENOIDS
MULTISUBSTITUTED OLEFINS
STEREOSPECIFIC SYNTHESIS
PLATFORM SYNTHESIS
INTERNAL ALKYNES
1,1-DICHLORO-1-ALKENES
ARYLBORONIC ACIDS
ORGANOBORONIC ACIDS
asymmetric synthesis
stereoselectivity
cross-coupling
HYDROARYLATION
olefination
CONJUGATE ADDITION
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Summary:The generation of a series of trisubstituted olefins bearing alkyl substituents is described using a stereoselective and regioselective addition to alkynyl esters. The method produces trisubstituted olefins as single isomers using a convenient and mild transformation in which alkyl boranes are cross-coupled with alkynyl esters and amides using palladium catalysis.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0030-1259933