Synthesis, resolution and absolute configuration of trans 4,5-diphenyl-pyrrolidin-2-one:: a possible chiral auxiliary

被引：16
作者：
Escalante, J [1 ]
González-Tototzin, MA [1 ]
机构：
[1] Univ Autonoma Estado Morelos, Ctr Invest Quim, Cuernavaca 62210, Morelos, Mexico
来源：
TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 08期
关键词：
D O I：
10.1016/S0957-4166(03)00097-1
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
beta-Lactam (+/-)-N-benzyl-4-phenyl-azetidin-2-one rac-6a was converted into the gamma-lactam (+/-)-traps-4,5-diphenyl-pyrrolidin-2-one rac-5 which was resolved via the preparation of diastereomers with N-phthalyl-L-alanine chloride or D-alanine chloride and its absolute configuration was determined by X-ray crystallographic analysis. This heterocycle has potential as a chiral gamma-lactam in asymmetric induction due to the steric effects of its phenyl groups. (C) 2003 Elsevier Science Ltd. All rights reserved.
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页码：981 / 985
页数：5
相关论文
共 22 条
  • [1] AHN C, 1999, J KOREAN CHEM SOC, V43, P489
  • [2] [Anonymous], [No title captured]
  • [3] BAEYER A, 1885, BER, P2269
  • [4] BROWN HC, 1975, ORGANIC SYNTHESIS VI, P256
  • [5] (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in the enantioselective preparation of α-amino acids
    Camps, P
    Pérez, F
    Soldevilla, N
    Borrego, MA
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (03) : 493 - 509
  • [6] SYNTHESIS OF 5-SUBSTITUTED-3,3-DIMETHYL-2-PYRROLIDINONES - QUAT CHIRAL AUXILIARIES
    DAVIES, SG
    DOISNEAU, GJM
    PRODGER, JC
    SANGANEE, HJ
    [J]. TETRAHEDRON LETTERS, 1994, 35 (15) : 2369 - 2372
  • [7] de Parrodi CA, 2001, TETRAHEDRON-ASYMMETR, V12, P69
  • [8] BASE-INDUCED RING ENLARGEMENTS OF 1-BENZYL-2-AZETIDINONES AND 1-ALLYL-2-AZETIDINONES
    DURST, T
    VANDENEL.R
    LEBELLE, MJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (26) : 9261 - 9263
  • [9] Synthesis of β-lactams and cyclo-β-dipeptides from β-amino acids:: experimental observations and theoretical analysis
    Escalante, J
    González-Tototzin, MA
    Aviña, J
    Muñoz-Muñiz, O
    Juaristi, E
    [J]. TETRAHEDRON, 2001, 57 (10) : 1883 - 1890
  • [10] Asymmetric Michael addition reactions using ethyl (S)-4,4-dimethylpyroglutamate as a chiral auxiliary
    Ezquerra, J
    Prieto, L
    Avendaño, C
    Martos, JL
    de la Cuesta, E
    [J]. TETRAHEDRON LETTERS, 1999, 40 (08) : 1575 - 1578
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