Literature DB >> 15255677

Asymmetric synthesis of quaternary alpha- and beta-amino acids and beta-lactams via proline-catalyzed mannich reactions with branched aldehyde donors.

Naidu S Chowdari1, Jeff T Suri, Carlos F Barbas.   

Abstract

[reaction: see text] L-Proline-catalyzed direct asymmetric Mannich reactions of N-PMP protected alpha-imino ethyl glyoxylate with various alpha,alpha-disubstituted aldehydes affords quaternary beta-formyl alpha-amino acid derivatives with excellent yields and enantioselectivities. The Mannich products are further converted to the corresponding quaternary alpha- and beta-amino acids and beta-lactams.

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Year:  2004        PMID: 15255677     DOI: 10.1021/ol049248+

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


  9 in total

1.  Catalytic asymmetric addition of dialkylzinc reagents to alpha-aldiminoesters.

Authors:  Sandeep Basra; Michael W Fennie; Marisa C Kozlowski
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

2.  Enantioselective Organocatalyzed Michael Addition of Isobutyraldehyde to Maleimides in Aqueous Media.

Authors:  Jae Ho Shim; Seok Hyun Cheun; Hyeon Soo Kim; Deok-Chan Ha
Journal:  Molecules       Date:  2022-04-25       Impact factor: 4.927

3.  Direct Catalytic Asymmetric Mannich Reactions for the Construction of Quaternary Carbon Stereocenters.

Authors:  Barry M Trost; Tanguy Saget; Chao-I Joey Hung
Journal:  J Am Chem Soc       Date:  2016-03-09       Impact factor: 15.419

4.  Synthesis and Deployment of an Elusive Fluorovinyl Cation Equivalent: Access to Quaternary α-(1'-Fluoro)vinyl Amino Acids as Potential PLP Enzyme Inactivators.

Authors:  Christopher D McCune; Matthew L Beio; Jill M Sturdivant; Roberto de la Salud-Bea; Brendan M Darnell; David B Berkowitz
Journal:  J Am Chem Soc       Date:  2017-09-28       Impact factor: 15.419

5.  Pipecolic acid-catalyzed direct asymmetric mannich reactions.

Authors:  Paul Ha-Yeon Cheong; Haile Zhang; Rajee Thayumanavan; Fujie Tanaka; K N Houk; Carlos F Barbas
Journal:  Org Lett       Date:  2006-03-02       Impact factor: 6.005

6.  Enantioselective synthesis of α-quaternary Mannich adducts by palladium-catalyzed allylic alkylation: total synthesis of (+)-sibirinine.

Authors:  Yoshitaka Numajiri; Beau P Pritchett; Koji Chiyoda; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2015-01-20       Impact factor: 15.419

7.  A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones.

Authors:  Jian-Xiong An; Fen-Fen Yang; Pan Wang; Zhi-Cheng Gu; Yan Li; Lei Chen; Yong-Long Zhao; Bin He
Journal:  RSC Adv       Date:  2022-03-02       Impact factor: 3.361

8.  Skeletally diverse small molecules using a build/couple/pair strategy.

Authors:  Takuya Uchida; Manuela Rodriquez; Stuart L Schreiber
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

9.  Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction.

Authors:  Yiwen Xiong; Haibo Mei; Lingmin Wu; Jianlin Han; Yi Pan; Guigen Li
Journal:  Beilstein J Org Chem       Date:  2014-03-13       Impact factor: 2.883

  9 in total

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