Bronsted acid-catalyzed imine amidation

被引:272
作者
Rowland, GB [1 ]
Zhang, HL [1 ]
Rowland, EB [1 ]
Chennamadhavuni, S [1 ]
Wang, Y [1 ]
Antilla, JC [1 ]
机构
[1] Univ Mississippi, Dept Chem & Biochem, University, MS 38677 USA
关键词
D O I
10.1021/ja0533085
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method for the Brønsted acid-catalyzed addition of amide nucleophiles to imines to produce protected aminal products is described. Simple Brønsted acids (phenyl phosphinic acid and trifluoromethanesulfonimide) were shown to be excellent catalysts, providing high yields of the aminal product. A catalytic asymmetric imine amidation using sulfonamides as nucleophiles was successful when a hindered biaryl phosphoric acid catalyst derived from 2,2′-diphenyl-[3,3′-biphenanthrene]-4,4′-diol (VAPOL) was used. Excellent yields and enantioselectivities were found in these additions (up to 99% ee). Copyright © 2005 American Chemical Society.
引用
收藏
页码:15696 / 15697
页数:2
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共 35 条
  • [1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
    Akiyama, T
    Itoh, J
    Yokota, K
    Fuchibe, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
  • [2] Synthesis, resolution, and determination of absolute configuration of a vaulted 2,2'-binaphthol and a vaulted 3,3'-biphenanthrol (VAPOL)
    Bao, JM
    Wulff, WD
    Dominy, JB
    Fumo, MJ
    Grant, EB
    Rob, AC
    Whitcomb, MC
    Yeung, SM
    Ostrander, RL
    Rheingold, AL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (14) : 3392 - 3405
  • [3] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity
    Bloch, R
    [J]. CHEMICAL REVIEWS, 1998, 98 (04) : 1407 - 1438
  • [4] A DOZEN YEARS OF RETRO-INVERSO PEPTIDOMIMETICS
    CHOREV, M
    GOODMAN, M
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (05) : 266 - 273
  • [5] In the golden age of organocatalysis
    Dalko, PI
    Moisan, L
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
  • [6] DERKACH NY, 1982, J ORG CHEM, V18, P60
  • [7] DIGREGORIO G, 1992, INNOVATION PERSPECTI, P311
  • [8] DRACH BS, 1975, J ORG CHEM, V11, P310
  • [9] DRACH BS, 1969, J ORG CHEM USSR, V5, P2117
  • [10] A NEW CLASS OF AMINO-ACID BASED SWEETENERS
    FULLER, WD
    GOODMAN, M
    VERLANDER, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (20) : 5821 - 5822