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Rhodium-Catalyzed Asymmetric Rearrangement of Alkynyl Alkenyl Carbinols: Synthetic Equivalent to Asymmetric Conjugate Alkynylation of Enones
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Section:Abstract
Asymmetric 1,3-rearrangement of an alkynyl group of alkynyl alkenyl carbinols giving β-alkynylketones took place in high yields with high enantioselectivity in the presence of a hydroxyrhodium/(R)-binap catalyst. The present method including a key β-alkynyl elimination step in the catalytic cycle is synthetically equivalent to the asymmetric conjugate addition of terminal alkynes to β-substituted enones.
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This article has been cited by 13 ACS Journal articles (5 most recent appear below).
Rate-Limiting Step of the Rh-Catalyzed Carboacylation of Alkenes: C–C Bond Activation or Migratory Insertion?
J. Patrick Lutz, Colin M. Rathbun, Susan M. Stevenson, Breanna M. Powell, Timothy S. Boman, Casey E. Baxter, John M. Zona, and Jeffrey B. JohnsonJournal of the American Chemical Society2012 134 (1), 715-722Rate-Limiting Step of the Rh-Catalyzed Carboacylation of Alkenes: C–C Bond Activation or Migratory Insertion?
J. Patrick Lutz, Colin M. Rathbun, Susan M. Stevenson, Breanna M. Powell, Timothy S. Boman, Casey E. Baxter, John M. Zona, and Jeffrey B. JohnsonJournal of the American Chemical Society2012 134 (1), 715-722Rhodium-catalyzed intramolecular carboacylation of alkenes, achieved using quinolinyl ketones containing tethered alkenes, proceeds via the activation and functionalization of a carbon–carbon single bond. This transformation has been demonstrated using ...
Enantioselective Synthesis of Alkyne-Substituted Quaternary Carbon Stereogenic Centers through NHC−Cu-Catalyzed Allylic Substitution Reactions with (i-Bu)2(Alkynyl)aluminum Reagents
Jennifer A. Dabrowski, Fang Gao, and Amir H. HoveydaJournal of the American Chemical Society2011 133 (13), 4778-4781Enantioselective Synthesis of Alkyne-Substituted Quaternary Carbon Stereogenic Centers through NHC−Cu-Catalyzed Allylic Substitution Reactions with (i-Bu)2(Alkynyl)aluminum Reagents
Jennifer A. Dabrowski, Fang Gao, and Amir H. HoveydaJournal of the American Chemical Society2011 133 (13), 4778-4781A catalytic enantioselective method for the formation of alkyne-substituted all-carbon quaternary stereogenic centers is reported. Additions of alkynylaluminums to alkyl-, aryl-, carboxylic ester-, or silyl-substituted allylic phosphates are promoted by ...
Rhodium(III)-Catalyzed Arylation of Boc-Imines via C−H Bond Functionalization
Andy S. Tsai, Michael E. Tauchert, Robert G. Bergman, and Jonathan A. EllmanJournal of the American Chemical Society2011 133 (5), 1248-1250Rhodium(III)-Catalyzed Arylation of Boc-Imines via C−H Bond Functionalization
Andy S. Tsai, Michael E. Tauchert, Robert G. Bergman, and Jonathan A. EllmanJournal of the American Chemical Society2011 133 (5), 1248-1250The first rhodium-catalyzed arylation of imines proceeding via C−H bond functionalization is reported. Use of a non-coordinating halide abstractor is important to obtain reactivity. Aryl-branched N-Boc-amines are formed, and a wide range of functionality ...
Practical Asymmetric Conjugate Alkynylation of Meldrum’s Acid-Derived Acceptors: Access to Chiral β-Alkynyl Acids
Sheng Cui, Shawn D. Walker, Jacqueline C. S. Woo, Christopher J. Borths, Herschel Mukherjee, Maosheng J. Chen and Margaret M. FaulJournal of the American Chemical Society2010 132 (2), 436-437Practical Asymmetric Conjugate Alkynylation of Meldrum’s Acid-Derived Acceptors: Access to Chiral β-Alkynyl Acids
Sheng Cui, Shawn D. Walker, Jacqueline C. S. Woo, Christopher J. Borths, Herschel Mukherjee, Maosheng J. Chen and Margaret M. FaulJournal of the American Chemical Society2010 132 (2), 436-437The enantioselective conjugate addition of alkynyl nucleophiles has been a long-standing challenge in synthetic chemistry. This paper describes a highly practical asymmetric conjugate alkynylation of Meldrum’s acid-derived acceptors using cinchonidine (<$...
Ni(II)-Catalyzed Enantioselective Conjugate Addition of Acetylenes to α,β-Enones
Oleg V. Larionov and E. J. CoreyOrganic Letters2010 12 (2), 300-302Ni(II)-Catalyzed Enantioselective Conjugate Addition of Acetylenes to α,β-Enones
Oleg V. Larionov and E. J. CoreyOrganic Letters2010 12 (2), 300-302Alkynylaluminum reagents undergo enantioselective conjugate addition to cyclic α,β-enones in the presence of chiral bisphosphine complexes of Ni(II).
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- Published In Issue November 21, 2007
- Received August 23, 2007
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