Direct asymmetric aldol reactions catalyzed by (4S)-phenoxy-(S)-proline

被引:0
|
作者
Shen, ZX [1 ]
Zhou, H [1 ]
Ma, JM [1 ]
Liu, YH [1 ]
Zhang, YW [1 ]
机构
[1] Suzhou Univ, Coll Chem & Chem Engn, Key Lab Organ Synth Jiangsu Prov, Suzhou 215006, Peoples R China
关键词
aldol reaction; catalysis; asymmetric;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Mitsunobu reaction of N-ethoxycarbonyl-(4R)-hydroxy-(S)-proline methyl ester with phenol afforded (4S)-phenoxy-(S)-proline methyl. ester, which, after saponification and hydrolysis in hydrochloric acid, gave the title amino acid. This compound (5 mol%) catalyzes aldol reaction of acetone with benzaldehydes enantioselectively in the yields ranging from 67.4% to 89.9%, with the ee up to 76.5%.
引用
收藏
页码:1213 / 1216
页数:4
相关论文
共 12 条
  • [1] Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions
    Hoang, L
    Bahmanyar, S
    Houk, KN
    List, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) : 16 - 17
  • [2] Catalytic asymmetric homo-aldol reaction of pyruvate - a chiral Lewis acid catalyst that mimics aldolase enzymes
    Juhl, K
    Gathergood, N
    Jorgensen, KA
    [J]. CHEMICAL COMMUNICATIONS, 2000, (22) : 2211 - 2212
  • [3] Proline-catalyzed asymmetric reactions
    List, B
    [J]. TETRAHEDRON, 2002, 58 (28) : 5573 - 5590
  • [4] Proline-catalyzed direct asymmetric aldol reactions
    List, B
    Lerner, RA
    Barbas, CF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) : 2395 - 2396
  • [5] Proline-catalyzed asymmetric aldol reactions between ketones and α-unsubstituted aldehydes
    List, B
    Pojarliev, P
    Castello, C
    [J]. ORGANIC LETTERS, 2001, 3 (04) : 573 - 575
  • [6] The first direct and enantioselective cross-aldol reaction of aldehydes
    Northrup, AB
    MacMillan, DWC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (24) : 6798 - 6799
  • [7] Amino acid catalyzed direct asymmetric aldol reactions: A bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions
    Sakthivel, K
    Notz, W
    Bui, T
    Barbas, CF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) : 5260 - 5267
  • [8] Novel small organic molecules for a highly enantioselective direct Aldol reaction
    Tang, Z
    Jiang, F
    Yu, LT
    Cui, X
    Gong, LZ
    Mi, AQ
    Jiang, YZ
    Wu, YD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (18) : 5262 - 5263
  • [9] Direct catalytic asymmetric aldol reactions promoted by a novel barium complex
    Yamada, YMA
    Shibasaki, M
    [J]. TETRAHEDRON LETTERS, 1998, 39 (31) : 5561 - 5564
  • [10] Direct catalytic asymmetric aldol reaction:: Synthesis of either syn- or anti-α,β-dihydroxy ketones
    Yoshikawa, N
    Kumagai, N
    Matsunaga, S
    Moll, G
    Ohshima, T
    Suzuki, T
    Shibasaki, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (10) : 2466 - 2467