Literature DB >> 26667068

Asymmetric Organocatalytic Reductive Coupling Reactions between Benzylidene Pyruvates and Aldehydes.

Matthew A Horwitz1, Blane P Zavesky1, Jesus I Martinez-Alvarado1, Jeffrey S Johnson1.   

Abstract

An organocatalytic three-component reductive coupling reaction between dimethyl phosphite, benzylidene pyruvates, and aldehydes is reported. A chiral triaryliminophosphorane catalyst promotes Pudovik addition, which is followed by phospha-Brook rearrangement to transiently generate enolates that are trapped stereoselectively by aldehydes. This reductive coupling provides vicinal polyfunctionalized stereocenters from readily available prochiral starting materials with excellent diastereoselectivity, enantioselectivity, and yield.

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Year:  2015        PMID： 26667068      PMCID： PMC4701628          DOI： 10.1021/acs.orglett.5b03127

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


  17 in total

1.  Stereoselective Cross Pinacol-Type Coupling between alpha,beta-Unsaturated Ketones and Aldehydes Mediated by Chromium(II) and R(3)SiCl Financial support by a Grant-in-Aid for Scientific Research on Priority Area No. 706 from the Ministry of Education, Culture, Sports, Science and Technology of Japan is gratefully acknowledged.

Authors:  Kazuhiko Takai; Ryotaro Morita; Chika Toratsu
Journal:  Angew Chem Int Ed Engl       Date:  2001-03-16       Impact factor: 15.336

2.  Generation of acyl anion equivalents from acylphosphonates via phosphonate-phosphate rearrangement: a highly practical method for cross-benzoin reaction.

Authors:  Ayhan S Demir; Omer Reis; A Ciğdem Iğdir; Ilker Esiringü; Serkan Eymur
Journal:  J Org Chem       Date:  2005-12-09       Impact factor: 4.354

3.  Base-catalyzed direct aldolization of α-alkyl-α-hydroxy trialkyl phosphonoacetates.

Authors:  Michael T Corbett; Daisuke Uraguchi; Takashi Ooi; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

4.  Samarium(II)-mediated pinacol coupling in water: occurrence of unexpected disproportionation and action of low-valent samarium as an active species.

Authors:  Satoru Matsukawa; Yumi Hinakubo
Journal:  Org Lett       Date:  2003-04-17       Impact factor: 6.005

5.  Highly enantioselective 1,4-addition of diethyl phosphite to enones using a dinuclear Zn catalyst.

Authors:  Depeng Zhao; Ye Yuan; Albert S C Chan; Rui Wang
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

6.  Zn/InCl(3)-mediated pinacol cross-coupling reactions of aldehydes with alpha,beta-unsaturated ketones in aqueous media.

Authors:  Yong-Sheng Yang; Zhi-Liang Shen; Teck-Peng Loh
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005

7.  Generation of chiral phosphonium dialkyl phosphite as a highly reactive P-nucleophile: application to asymmetric hydrophosphonylation of aldehydes.

Authors:  Daisuke Uraguchi; Takaki Ito; Takashi Ooi
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419

8.  Reductive homocondensation of benzylidene- and alkylidenepyruvate esters by a P(NMe2)3-mediated tandem reaction.

Authors:  Sunewang Rixin Wang; Alexander T Radosevich
Journal:  Org Lett       Date:  2013-04-11       Impact factor: 6.005

9.  Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction.

Authors:  Marta G Núñez; Alistair J M Farley; Darren J Dixon
Journal:  J Am Chem Soc       Date:  2013-11-06       Impact factor: 15.419

10.  Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes.

Authors:  Matthew A Horwitz; Naoya Tanaka; Takuya Yokosaka; Daisuke Uraguchi; Jeffrey S Johnson; Takashi Ooi
Journal:  Chem Sci       Date:  2015-07-30       Impact factor: 9.825
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  11 in total

Review 1.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

2.  2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

Authors:  Kangnan Li; Xinxin Shao; Luke Tseng; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-01-04       Impact factor: 15.419

3.  Asymmetric Organocatalytic Sulfa-Michael Addition to Enone Diesters.

Authors:  Jennifer L Fulton; Matthew A Horwitz; Ericka L Bruske; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2018-03-07       Impact factor: 4.354

4.  Enantio- and Diastereoselective Organocatalytic Conjugate Additions of Nitroalkanes to Enone Diesters.

Authors:  Matthew A Horwitz; Jennifer L Fulton; Jeffrey S Johnson
Journal:  Org Lett       Date:  2017-11-03       Impact factor: 6.005

5.  Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters.

Authors:  Jessica A Griswold; Matthew A Horwitz; Leslie V Leiva; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2017-02-06       Impact factor: 4.354

6.  Palladium-Catalyzed β-Arylation of α-Keto Esters.

Authors:  Blane P Zavesky; Samuel L Bartlett; Jeffrey S Johnson
Journal:  Org Lett       Date:  2017-04-11       Impact factor: 6.005

7.  Phosphite-Mediated Reductive Cross-Coupling of Isatins and Nitrostyrenes.

Authors:  Somayeh Motevalli; Jeffrey S Johnson
Journal:  Synthesis (Stuttg)       Date:  2017-05-02       Impact factor: 3.157

8.  Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition.

Authors:  Matthew A Horwitz; Elisabetta Massolo; Jeffrey S Johnson
Journal:  Beilstein J Org Chem       Date:  2017-04-24       Impact factor: 2.883

9.  Enantioselective bifunctional iminophosphorane catalyzed sulfa-Michael addition of alkyl thiols to unactivated β-substituted-α,β-unsaturated esters.

Authors:  Jinchao Yang; Alistair J M Farley; Darren J Dixon
Journal:  Chem Sci       Date:  2016-09-14       Impact factor: 9.825

10.  Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles.

Authors:  Michele Formica; Geoffroy Sorin; Alistair J M Farley; Jesús Díaz; Robert S Paton; Darren J Dixon
Journal:  Chem Sci       Date:  2018-07-23       Impact factor: 9.825
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