Literature DB >> 19373816

Diastereoselective synthesis of pentasubstituted gamma-butyrolactones from silyl glyoxylates and ketones through a double Reformatsky reaction.

Stephen N Greszler1, Jeffrey S Johnson.   

Abstract

Three contiguous stereocenters can be established with remarkable diastereoselectivity in a double Reformatsky sequence. Densely functionalized gamma-butyrolactones were assembled rapidly by this approach, in which a ketone is used as the terminal electrophile (see scheme). Secondary transformations of the lactone products enhance their synthetic utility. R(1) = Me, H; R(2) = alkyl, aryl, CF(3); Bn = benzyl, TBS = tert-butyldimethylsilyl.

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Year:  2009        PMID： 19373816      PMCID： PMC2801152          DOI： 10.1002/anie.200900215

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


  14 in total

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2.  Reformatsky reactions meet catalysis and stereoselectivity.

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Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  A catalytic, Me2Zn-mediated, enantioselective reformatsky reaction with ketones.

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Journal:  Angew Chem Int Ed Engl       Date:  2006-04-28       Impact factor: 15.336

4.  Catalytic enantioselective Reformatsky reaction with ketones.

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Journal:  J Am Chem Soc       Date:  2006-12-13       Impact factor: 15.419

6.  Three-component coupling reactions of silylglyoxylates, alkynes, and aldehydes: a chemoselective one-step glycolate aldol construction.

Authors:  David A Nicewicz; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2005-05-04       Impact factor: 15.419

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8.  [3 + 2] Annulation of beta-heteroatom-substituted alpha,beta-unsaturated acylsilanes with methyl ketone enolates: scope and investigation of the reaction course.

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Journal:  J Org Chem       Date:  2002-03-22       Impact factor: 4.354

9.  Highly stereoselective synthesis of substituted gamma-lactams from acylsilanes.

Authors:  Robert B Lettan; Chase C Woodward; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  Catalytic enantioselective Reformatsky reaction with ortho-substituted diarylketones.

Authors:  M Angeles Fernández-Ibáñez; Beatriz Maciá; Adriaan J Minnaard; Ben L Feringa
Journal:  Org Lett       Date:  2008-08-21       Impact factor: 6.005
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  10 in total

1.  Catalytic nucleophilic glyoxylation of aldehydes.

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Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

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Journal:  Org Lett       Date:  2011-08-31       Impact factor: 6.005

3.  Three-component glycolate Michael reactions of enolates, silyl glyoxylates, and α,β-enones.

Authors:  Daniel C Schmitt; Ericka J Malow; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2012-03-15       Impact factor: 4.354

4.  Synthesis of gamma,delta-unsaturated glycolic acids via sequenced brook and Ireland--claisen rearrangements.

Authors:  Daniel C Schmitt; Jeffrey S Johnson
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

5.  On-demand synthesis of organozinc halides under continuous flow conditions.

Authors:  Mateo Berton; Lena Huck; Jesús Alcázar
Journal:  Nat Protoc       Date:  2018-01-11       Impact factor: 13.491

6.  Construction of cyclopentanol derivatives via three-component coupling of silyl glyoxylates, acetylides, and nitroalkenes.

Authors:  Gregory R Boyce; Shubin Liu; Jeffrey S Johnson
Journal:  Org Lett       Date:  2012-01-11       Impact factor: 6.005

7.  Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

Authors:  Gregory R Boyce; Stephen N Greszler; Jeffrey S Johnson; Xin Linghu; Justin T Malinowski; David A Nicewicz; Andrew D Satterfield; Daniel C Schmitt; Kimberly M Steward
Journal:  J Org Chem       Date:  2012-03-23       Impact factor: 4.354

8.  Remote stereoinduction in the acylation of fully substituted enolates: tandem Reformatsky/quaternary Claisen condensations of silyl glyoxylates and β-lactones.

Authors:  Stephen N Greszler; Justin T Malinowski; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2010-11-18       Impact factor: 15.419

9.  Electroreductive coupling of 2-acylbenzoates with α,β-unsaturated carbonyl compounds: density functional theory study on product selectivity.

Authors:  Naoki Kise; Toshihiko Sakurai
Journal:  Beilstein J Org Chem       Date:  2022-08-02       Impact factor: 2.544

10.  Alternaric acid: formal synthesis and related studies.

Authors:  Michael C Slade; Jeffrey S Johnson
Journal:  Beilstein J Org Chem       Date:  2013-01-24       Impact factor: 2.883
  10 in total

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