Literature DB >> 17887693

A catalytic asymmetric vinylogous Mukaiyama aldol reaction.

Lars V Heumann1, Gary E Keck.   

Abstract

A vinylogous Mukaiyama aldol reaction, conducted using 10 mol % of a BITIP catalyst and B(OMe)3 as an additive, effects an enantioselective four-carbon chain extension to give versatile E-alpha,beta-unsaturated thiol esters.

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Year:  2007        PMID： 17887693      PMCID： PMC2516376          DOI： 10.1021/ol701851f

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  16 in total

1.  The Catalytic Asymmetric Aldol Reaction.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-04       Impact factor: 15.336

2.  Asymmetric Total Synthesis of Rhizoxin D Financial support has been provided by the National Institutes of Health (through grant GM-28961) and by Pfizer, Inc.

Authors:  Gary E. Keck; Carrie A. Wager; Travis T. Wager; Kenneth A. Savin; Jonathan A. Covel; Mark D. McLaws; Dhileep Krishnamurthy; Victor J. Cee
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-05       Impact factor: 15.336

3.  Stereocontrolled total synthesis of (-)-aurisides A and B.

Authors:  Ian Paterson; Gordon J Florence; Annekatrin C Heimann; Angela C Mackay
Journal:  Angew Chem Int Ed Engl       Date:  2005-02-04       Impact factor: 15.336

Review 4.  BINOL: a versatile chiral reagent.

Authors:  Jean Michel Brunel
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

5.  Lewis Acid-Promoted, Stereocontrolled, Gram Scale, Diels-Alder Cycloadditions of Electronically Matched 2-Pyrones and Vinyl Ethers: The Critical Importance of Molecular Sieves and the Temperature of Titanium Coordination with the Pyrone.

Authors:  Gary H. Posner; Haiyan Dai; D. Scott Bull; Jae-Kyoo Lee; Franck Eydoux; Yuji Ishihara; William Welsh; Neil Pryor; Stan Petr
Journal:  J Org Chem       Date:  1996-01-26       Impact factor: 4.354

6.  Snapshots of titanium BINOLate complexes with diverse solid state structures.

Authors:  T J Davis; J Balsells; P J Carroll; P J Walsh
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

7.  Enantio- and diastereoselective additions to aldehydes using the bifunctional reagent 2-(chloromethyl)-3-(tributylstannyl)propene: application to a synthesis of the C16-C27 segment of bryostatin 1.

Authors:  Gary E Keck; Tao Yu; Mark D McLaws
Journal:  J Org Chem       Date:  2005-04-01       Impact factor: 4.354

8.  Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.

Authors:  Gary E Keck; Jonathan A Covel; Tobias Schiff; Tao Yu
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

Review 9.  Catalytic, enantioselective, vinylogous aldol reactions.

Authors:  Scott E Denmark; John R Heemstra; Gregory L Beutner
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-25       Impact factor: 15.336

10.  Insight into the mechanism of the asymmetric addition of alkyl groups to aldehydes catalyzed by titanium-BINOLate species.

Authors:  Jaume Balsells; Timothy J Davis; Patrick Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2002-09-04       Impact factor: 15.419
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  2 in total

1.  Enantioselective iridium-catalyzed vinylogous Reformatsky-aldol reaction from the alcohol oxidation level: linear regioselectivity by way of carbon-bound enolates.

Authors:  Abbas Hassan; Jason R Zbieg; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-04       Impact factor: 15.336

2.  A new method for the synthesis of H(4)-BINOL.

Authors:  Lars V Heumann; Gary E Keck
Journal:  J Org Chem       Date:  2008-05-20       Impact factor: 4.354
  2 in total

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