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A Highly Stereoselective TMSOTf-Mediated Catalytic Carbocupration of Alkynoates
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Section:Abstract
The TMSOTf-mediated catalytic carbocupration of ynoates has been investigated. It has been shown that catalyst loadings as low as 5 mol % readily allow for high yields and diastereoselectivities for a series of aromatic Grignard reagents. In addition, we have been successful in vicinally functionalizing 1a via initial TMSOTf-mediated catalytic carbocupration followed by a secondary electrophilic capture of the TMS allenoate intermediate.
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
Highly Z-Selective Asymmetric 1,4-Addition Reaction of 5H-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines
Tomonori Misaki, Kei Kawano, and Takashi SugimuraJournal of the American Chemical Society2011 133 (15), 5695-5697Highly Z-Selective Asymmetric 1,4-Addition Reaction of 5H-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines
Tomonori Misaki, Kei Kawano, and Takashi SugimuraJournal of the American Chemical Society2011 133 (15), 5695-5697An asymmetric 1,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds was developed, and, for the first time, high enantiomeric and geometric control was achieved to afford the thermodynamically unstable Z-isomer predominantly using ...
Vicinal Functionalization of Propiolate Esters via Catalytic Carbocupration: Stereoselective Formation of Substituted Vinyl Silanes
Amanda J. Mueller Hendrix and Michael P. JenningsOrganic Letters2010 12 (12), 2750-2753Vicinal Functionalization of Propiolate Esters via Catalytic Carbocupration: Stereoselective Formation of Substituted Vinyl Silanes
Amanda J. Mueller Hendrix and Michael P. JenningsOrganic Letters2010 12 (12), 2750-2753The vicinal functionalization of propiolate esters via a catalytic carbocupration−silicon group migration sequence has been investigated. We have observed that catalyst loadings as low as 5 mol % allow for good yields and excellent ...
Highly Selective α-Acylvinyl Anion Additions to Imines
Troy E. Reynolds, Michael S. Binkley and Karl A. ScheidtOrganic Letters2008 10 (22), 5227-5230Highly Selective α-Acylvinyl Anion Additions to Imines
Troy E. Reynolds, Michael S. Binkley and Karl A. ScheidtOrganic Letters2008 10 (22), 5227-5230α-Hydroxypropargylsilanes undergo rearrangement to form reactive lithium allenolates. The resulting α-acylvinyl anion equivalents undergo highly selective additions to N-tert-butanesulfinyl imines generating β-substituted aza-MBH-type products. High ...
Lewis Acid-Catalyzed Conjugate Additions of Silyloxyallenes: A Selective Solution to the Intermolecular Rauhut−Currier Problem
Troy E. Reynolds, Michael S. Binkley and Karl A. ScheidtOrganic Letters2008 10 (12), 2449-2452Lewis Acid-Catalyzed Conjugate Additions of Silyloxyallenes: A Selective Solution to the Intermolecular Rauhut−Currier Problem
Troy E. Reynolds, Michael S. Binkley and Karl A. ScheidtOrganic Letters2008 10 (12), 2449-2452Silyloxyallenes serve as highly useful α-acylvinyl anion equivalents. These latent allenolates undergo conjugate additions to alkylidene malonates in the presence of 10 mol % Sc(OTf)3. The reaction delivers intermolecular Rauhut−Currier products in ...
Vicinal Functionalization of Propiolate Esters via a Tandem Catalytic Carbocupration−Mukaiyama Aldol Reaction Sequence
Amanda J. Mueller and Michael P. JenningsOrganic Letters2008 10 (8), 1649-1652Vicinal Functionalization of Propiolate Esters via a Tandem Catalytic Carbocupration−Mukaiyama Aldol Reaction Sequence
Amanda J. Mueller and Michael P. JenningsOrganic Letters2008 10 (8), 1649-1652The vicinal functionalization of propiolate esters via a tandem catalytic carbocuprationMukaiyama aldol reaction sequence has been investigated. It has been shown that catalyst loadings as low as 8 mol % readily allow for good yields and excellent ...
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History
- Published In Issue December 06, 2007
- Received October 30, 2007
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