Literature DB >> 18683828

Enantioselective synthesis of all-carbon quaternary stereogenic centers by catalytic asymmetric conjugate additions of alkyl and aryl aluminum reagents to five-, six-, and seven-membered-ring beta-substituted cyclic enones.

Tricia L May1, M Kevin Brown, Amir H Hoveyda.   

Abstract

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Year:  2008        PMID： 18683828      PMCID： PMC2737810          DOI： 10.1002/anie.200802910

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


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  19 in total

1.  Modular peptide-based phosphine ligands in asymmetric catalysis: efficient and enantioselective Cu-catalyzed conjugate additions to five-, six-, and seven-membered cyclic enones.

Authors:  S J Degrado; H Mizutani; A H Hoveyda
Journal:  J Am Chem Soc       Date:  2001-01-31       Impact factor: 15.419

2.  Bidentate NHC-based chiral ligands for efficient Cu-catalyzed enantioselective allylic alkylations: structure and activity of an air-stable chiral Cu complex.

Authors:  Andrew O Larsen; Wenhao Leu; Christina Nieto Oberhuber; John E Campbell; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2004-09-15       Impact factor: 15.419

3.  New general sulfinylating process for asymmetric synthesis of enantiopure sulfinates and sulfoxides.

Authors:  Bruce Z Lu; Fuqiang Jin; Yongda Zhang; Xinhe Wu; Stephen A Wald; Chris H Senanayake
Journal:  Org Lett       Date:  2005-04-14       Impact factor: 6.005

4.  Highly site- and enantioselective Cu-catalyzed allylic alkylation reactions with easily accessible vinylaluminum reagents.

Authors:  Yunmi Lee; Katsuhiro Akiyama; Dennis G Gillingham; M Kevin Brown; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2007-12-19       Impact factor: 15.419

5.  A practical method for enantioselective synthesis of all-carbon quaternary stereogenic centers through NHC-Cu-catalyzed conjugate additions of alkyl- and arylzinc reagents to beta-substituted cyclic enones.

Authors:  Kang-sang Lee; M Kevin Brown; Alexander W Hird; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2006-06-07       Impact factor: 15.419

6.  Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers.

Authors:  David Martin; Stefan Kehrli; Magali d'Augustin; Hervé Clavier; Marc Mauduit; Alexandre Alexakis
Journal:  J Am Chem Soc       Date:  2006-07-05       Impact factor: 15.419

7.  Lewis base activation of grignard reagents with N-heterocyclic carbenes. Cu-free catalytic enantioselective additions to gamma-chloro-alpha,beta-unsaturated esters.

Authors:  Yunmi Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2006-12-13       Impact factor: 15.419

8.  Highly enantioselective 1,4-addition of diorganozinc reagents to cyclic enones using chiral diphosphite ligands derived from H8-binaphthol.

Authors:  Liang Liang; Terry T L Au-Yeung; Albert S C Chan
Journal:  Org Lett       Date:  2002-10-31       Impact factor: 6.005

9.  Asymmetric synthesis of carboxylic acid derivatives having an all-carbon alpha-quaternary center through Cu-catalyzed 1,4-addition of dialkylzinc reagents to 2-aryl acetate derivatives.

Authors:  Ashraf Wilsily; Eric Fillion
Journal:  Org Lett       Date:  2008-05-30       Impact factor: 6.005

10.  Copper-catalyzed asymmetric conjugate addition of trialkylaluminium reagents to trisubstituted enones: construction of chiral quaternary centers.

Authors:  Magali Vuagnoux-d'Augustin; Alexandre Alexakis
Journal:  Chemistry       Date:  2007       Impact factor: 5.236
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  35 in total

1.  Mechanism and enantioselectivity in palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones: insights from computation and experiment.

Authors:  Jeffrey C Holder; Lufeng Zou; Alexander N Marziale; Peng Liu; Yu Lan; Michele Gatti; Kotaro Kikushima; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-09-27       Impact factor: 15.419

2.  Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered β-substituted cyclic enones: enantioselective construction of all-carbon quaternary stereocenters.

Authors:  Kotaro Kikushima; Jeffrey C Holder; Michele Gatti; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2011-04-15       Impact factor: 15.419

3.  Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents.

Authors:  Rebecca M Maksymowicz; Philippe M C Roth; Stephen P Fletcher
Journal:  Nat Chem       Date:  2012-07-15       Impact factor: 24.427

4.  Copper-catalyzed asymmetric conjugate addition of alkylzirconium reagents to cyclic enones to form quaternary centers.

Authors:  Philippe M C Roth; Mireia Sidera; Rebecca M Maksymowicz; Stephen P Fletcher
Journal:  Nat Protoc       Date:  2013-12-12       Impact factor: 13.491

5.  Enantioselective synthesis of allylboronates bearing a tertiary or quaternary B-substituted stereogenic carbon by NHC-Cu-catalyzed substitution reactions.

Authors:  Aikomari Guzman-Martinez; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-08-11       Impact factor: 15.419

6.  Enantioselective synthesis of boron-substituted quaternary carbons by NHC-Cu-catalyzed boronate conjugate additions to unsaturated carboxylic esters, ketones, or thioesters.

Authors:  Jeannette M O'Brien; Kang-sang Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-08-11       Impact factor: 15.419

7.  Synthesis of diverse β-quaternary ketones via palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enones.

Authors:  Jeffrey C Holder; Emmett D Goodman; Kotaro Kikushima; Michele Gatti; Alexander N Marziale; Brian M Stoltz
Journal:  Tetrahedron       Date:  2014-11-28       Impact factor: 2.457

8.  Preparation of (S)-tert-ButylPyOx and Palladium-catalyzed Asymmetric Conjugate Addition of Arylboronic Acids.

Authors:  Jeffrey C Holder; Samantha E Shockley; Mario P Wiesenfeldt; Hideki Shimizu; Brian M Stoltz
Journal:  Organic Synth       Date:  2016-03-04

Review 9.  Catalytic enantioselective olefin metathesis in natural product synthesis. Chiral metal-based complexes that deliver high enantioselectivity and more.

Authors:  Amir H Hoveyda; Steven J Malcolmson; Simon J Meek; Adil R Zhugralin
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

10.  Stereogenic-at-metal Zn- and Al-based N-heterocyclic carbene (NHC) complexes as bifunctional catalysts in Cu-free enantioselective allylic alkylations.

Authors:  Yunmi Lee; Bo Li; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-08-19       Impact factor: 15.419
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