Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions

被引:506
作者
Cobb, AJA [1 ]
Shaw, DM [1 ]
Longbottom, DA [1 ]
Gold, JB [1 ]
Ley, SV [1 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
关键词
D O I
10.1039/b414742a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tetrazole and acylsulfonamide organocatalysts derived from proline have been synthesised and applied to the asymmetric Mannich, nitro-Michael and aldol reactions to give results that are superior to the proline-catalysed counterpart.
引用
收藏
页码:84 / 96
页数:13
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共 70 条
  • [1] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF PENTAPEPTIDE ANALOGS OF THE POTENT ANGIOTENSIN CONVERTING ENZYME-INHIBITOR 5(S)-BENZAMIDO-4-OXO-6-PHENYLHEXANOYL-L-PROLINE
    ALMQUIST, RG
    JENNINGSWHITE, C
    CHAO, WR
    STEEGER, T
    WHEELER, K
    ROGERS, J
    MITOMA, C
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (08) : 1062 - 1066
  • [2] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions
    Bahmanyar, S
    Houk, KN
    Martin, HJ
    List, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) : 2475 - 2479
  • [3] The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions
    Bahmanyar, S
    Houk, KN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) : 12911 - 12912
  • [4] Proline-derived N-sullfonylcarboxamides:: Readily available, highly enantioselective and versatile catalysts for direct aldol reactions
    Berkessel, A
    Koch, B
    Lex, J
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1141 - 1146
  • [5] Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins
    Betancort, JM
    Sakthivel, K
    Thayumanavan, R
    Tanaka, F
    Barbas, CF
    [J]. SYNTHESIS-STUTTGART, 2004, (09): : 1509 - 1521
  • [6] ASYMMETRIC MICHAEL-ADDITIONS - PRACTICALLY COMPLETELY DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ALKYLATIONS OF THE ENAMINE FROM CYCLOHEXANONE AND PROLINYL METHYL-ETHER BY OMEGA-NITROSTYRENES TO GIVE U- 2-(1'-ARYL-2'-NITROETHYL)CYCLOHEXANONES
    BLARER, SJ
    SCHWEIZER, WB
    SEEBACH, D
    [J]. HELVETICA CHIMICA ACTA, 1982, 65 (05) : 1637 - 1654
  • [7] Direct catalytic asymmetric aldol reactions of aldehydes
    Bogevig, A
    Kumaragurubaran, N
    Jorgensen, KA
    [J]. CHEMICAL COMMUNICATIONS, 2002, (06) : 620 - 621
  • [8] Dynamic kinetic resolution of atropisomeric amides
    Chan, V
    Kim, JG
    Jimeno, C
    Carroll, PJ
    Walsh, PJ
    [J]. ORGANIC LETTERS, 2004, 6 (12) : 2051 - 2053
  • [9] Chowdari NS, 2003, SYNLETT, P1906
  • [10] 5-Pyrrolidin-2-yltetrazole as an asymmetric organocatalyst for the addition of ketones to nitro-olefins
    Cobb, AJA
    Longbottom, DA
    Shaw, DM
    Ley, SV
    [J]. CHEMICAL COMMUNICATIONS, 2004, (16) : 1808 - 1809