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Highly Stereoselective Synthesis of cis-Alkenyl Pinacolboronates and Potassium cis-Alkenyltrifluoroborates via a Hydroboration/ Protodeboronation Approach
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Abstract
A number of alkynyl pinacolboronates bearing various functional groups were synthesized according to literature methods. These were then stereoselectively reduced to the cis-alkenyl pinacolboronates via hydroboration with dicyclohexylborane followed by chemoselective protodeboronation using acetic acid. Treatment with potassium hydrogen fluoride smoothly converted these to the corresponding potassium organotrifluoroborates.
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This article has been cited by 7 ACS Journal articles (5 most recent appear below).
Hydride as a Leaving Group in the Reaction of Pinacolborane with Halides under Ambient Grignard and Barbier Conditions. One-Pot Synthesis of Alkyl, Aryl, Heteroaryl, Vinyl, and Allyl Pinacolboronic Esters
Jacob W. Clary, Terry J. Rettenmaier, Rachel Snelling, Whitney Bryks, Jesse Banwell, W. Todd Wipke, and Bakthan SingaramThe Journal of Organic Chemistry2011 76 (23), 9602-9610Hydride as a Leaving Group in the Reaction of Pinacolborane with Halides under Ambient Grignard and Barbier Conditions. One-Pot Synthesis of Alkyl, Aryl, Heteroaryl, Vinyl, and Allyl Pinacolboronic Esters
Jacob W. Clary, Terry J. Rettenmaier, Rachel Snelling, Whitney Bryks, Jesse Banwell, W. Todd Wipke, and Bakthan SingaramThe Journal of Organic Chemistry2011 76 (23), 9602-9610Grignard reagents (aliphatic, aromatic, heteroaromatic, vinyl, or allylic) react with 1 equiv of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolborane, PinBH) at ambient temperature in tetrahydrofuran (THF) to afford the corresponding pinacolboronates. ...
Total Synthesis of (±)-Cortistatin J from Furan
Mark G. Nilson and Raymond L. FunkJournal of the American Chemical Society2011 Article ASAPTotal Synthesis of (±)-Cortistatin J from Furan
Mark G. Nilson and Raymond L. FunkJournal of the American Chemical Society2011 Article ASAPA concise, diastereoselective total synthesis of (±)-cortistatin J has been completed in 20 steps from furan. Key steps include an intramolecular [4 + 3] cyclization of a disubstituted furan with a (Z)-2-(trialkylsilyloxy)-2-enal to construct the ...
An Opportunity for Mg-Catalyzed Grignard-Type Reactions: Direct Coupling of Benzylic Halides with Pinacolborane with 10 mol % of Magnesium
Christine Pintaric, Sandra Olivero, Yves Gimbert, Pierre Y. Chavant and Elisabet DuñachJournal of the American Chemical Society2010 132 (34), 11825-11827An Opportunity for Mg-Catalyzed Grignard-Type Reactions: Direct Coupling of Benzylic Halides with Pinacolborane with 10 mol % of Magnesium
Christine Pintaric, Sandra Olivero, Yves Gimbert, Pierre Y. Chavant and Elisabet DuñachJournal of the American Chemical Society2010 132 (34), 11825-11827Mg in catalytic amounts as the only metal permits the reductive coupling between benzyl halides and pinacolborane. HBpin acts both as an electrophile and as a reducing agent to regenerate an organomagnesium species in situ. An hydride oxidation mechanism ...
One-Pot Multicomponent Coupling Methods for the Synthesis of Diastereo- and Enantioenriched (Z)-Trisubstituted Allylic Alcohols
Michael H. Kerrigan, Sang-Jin Jeon, Young K. Chen, Luca Salvi, Patrick J. Carroll and Patrick J. WalshJournal of the American Chemical Society2009 131 (24), 8434-8445One-Pot Multicomponent Coupling Methods for the Synthesis of Diastereo- and Enantioenriched (Z)-Trisubstituted Allylic Alcohols
Michael H. Kerrigan, Sang-Jin Jeon, Young K. Chen, Luca Salvi, Patrick J. Carroll and Patrick J. WalshJournal of the American Chemical Society2009 131 (24), 8434-8445(Z)-Trisubstituted allylic alcohols are widespread structural motifs in natural products and biologically active compounds but are difficult to directly prepare. Introduced herein is a general one-pot multicomponent coupling method for the synthesis of (Z)...
Applications of 1-Alkenyl-1,1-Heterobimetallics in the Stereoselective Synthesis of Cyclopropylboronate Esters, Trisubstituted Cyclopropanols and 2,3-Disubstituted Cyclobutanones
Mahmud M. Hussain, Hongmei Li, Nusrah Hussain, Mercedes Ureña, Patrick J. Carroll and Patrick J. WalshJournal of the American Chemical Society2009 131 (18), 6516-6524Applications of 1-Alkenyl-1,1-Heterobimetallics in the Stereoselective Synthesis of Cyclopropylboronate Esters, Trisubstituted Cyclopropanols and 2,3-Disubstituted Cyclobutanones
Mahmud M. Hussain, Hongmei Li, Nusrah Hussain, Mercedes Ureña, Patrick J. Carroll and Patrick J. WalshJournal of the American Chemical Society2009 131 (18), 6516-65241-Alkenyl-1,1-heterobimetallics are potentially very useful in stereoselective organic synthesis but are relatively unexplored. Introduced herein is a practical application of 1-alkenyl-1,1-heterobimetallic intermediates in the synthesis of versatile ...
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History
- Published In Issue September 05, 2008
- Article ASAPAugust 06, 2008
- Received: June 2, 2008
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