Literature DB >> 29711311

Catalytic Enantioselective Aza Diels-Alder Reactions of Imino Dienophiles.

Sulan Yao1, Mogens Johannsen1, Rita G Hazell1, Karl Anker Jørgensen1.   

Abstract

1 mol% of catalyst is sufficient: The hetero Diels-Alder reaction of α-imino esters 1 with activated conjugated dienes 2 (R=H, Me) needs only 1 mol% of a 2,2'-bis(diarylphosphanyl)-1,1'-binaphthyl (BINAP) copper(I) complex as the catalyst to generate the adducts 3 in good yields and with enantioselectivities up to 96%. The reaction can also be carried out on gram scale! Tos=H3 CC6 H4 SO2 ; TMS=Me3 Si. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Asymmetric catalysis; Copper; Cycloadditions; Lewis acids; Synthetic methods

Year:  1998        PMID: 29711311     DOI: 10.1002/(SICI)1521-3773(19981204)37:22<3121::AID-ANIE3121>3.0.CO;2-J

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


  2 in total

1.  A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions.

Authors:  Patrick J Walsh; Hongmei Li; Cecilia Anaya de Parrodi
Journal:  Chem Rev       Date:  2007-05-27       Impact factor: 60.622

2.  Regulation of orthogonal functions in a dual catalyst system. Subservient role of a nonchiral Lewis acid in an asymmetric catalytic heteroatom Diels-Alder reaction.

Authors:  Cory A Newman; Jon C Antilla; Pei Chen; Alexander V Predeus; Lee Fielding; William D Wulff
Journal:  J Am Chem Soc       Date:  2007-05-16       Impact factor: 15.419

  2 in total

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