Synthetic studies on tetrazomine:: lipase PS resolution of racemic cis-β-hydroxypipecolic acid

被引:32
|
作者
Scott, JD [1 ]
Williams, RM [1 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(00)01527-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient enzymatic resolution of racemic cis-beta -hydroxypipecolic acid is described affording both the (2S,3R) and (2R,3S) protected amino acids in good yield and high enantiomeric ratios. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8413 / 8416
页数:4
相关论文
共 50 条
  • [21] A Stereoselective Route to cis-(2S,3R)-3-Hydroxypipecolic Acid and Two Enantiomeric cis-2-Hydroxymethyl-3-hydroxypiperidine Derivatives
    Chattopadhyay, Shital K.
    Roy, Shankar P.
    Saha, Tapan
    SYNTHESIS-STUTTGART, 2011, (16): : 2664 - 2670
  • [22] THE INFLUENCE OF PROTECTING GROUPS ON LIPASE-CATALYZED TRANSESTERIFICATIONS - ENZYMATIC RESOLUTION OF RACEMIC CIS-1,3-CYCLOPENTANEDIOL DERIVATIVES
    HENLY, R
    ELIE, CJJ
    BUSER, HP
    RAMOS, G
    MOSER, HE
    TETRAHEDRON LETTERS, 1993, 34 (18) : 2923 - 2926
  • [23] Efficient Resolution of cis-(±)-Dimethyl 1-Acetylpiperidine-2,3-dicarboxylate with Soluble Candida antarctica Lipase B (CAL B)
    Ramesh, Perla
    Harini, Tirunagari
    Fadnavis, Nitin W.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (01) : 296 - 301
  • [24] Resolution of N-protected cis- and trans-3-aminocyclohexanols via lipase-catalyzed enantioselective acylation in organic media
    Levy, LM
    de Gonzalo, G
    Gotor, V
    TETRAHEDRON-ASYMMETRY, 2004, 15 (13) : 2051 - 2056
  • [25] Synthesis of both enantiomers of cis-α-irone and cis-γ-irone, principal constituents of iris oil, via resolution of (±)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acid
    Inoue, T
    Kiyota, H
    Oritani, T
    TETRAHEDRON-ASYMMETRY, 2000, 11 (18) : 3807 - 3818
  • [26] Synthesis of (1R,cis,αS)-cypermethrine via lipase catalyzed kinetic resolution of racemic m-phenoxybenzaldehyde cyanohydrin acetate
    Roos, J
    Stelzer, U
    Effenberger, F
    TETRAHEDRON-ASYMMETRY, 1998, 9 (06) : 1043 - 1049
  • [27] Optical resolution of racemic 2-hydroxy octanoic acid by lipase-catalyzed hydrolysis in a biphasic membrane reactor
    Sakaki, K
    Itoh, N
    BIOTECHNOLOGY LETTERS, 2003, 25 (19) : 1591 - 1595
  • [28] Optical resolution of racemic 2-hydroxy octanoic acid by lipase-catalyzed hydrolysis in a biphasic membrane reactor
    Keiji Sakaki
    Naotsugu Itoh
    Biotechnology Letters, 2003, 25 : 1591 - 1595
  • [29] Resolution of racemic cis-1-amino-2-indanol by diastereomeric salt formation with (S)-2-phenylpropionic acid
    Sakurai, R
    Sakai, K
    TETRAHEDRON-ASYMMETRY, 2003, 14 (04) : 411 - 413
  • [30] Synthesis and conformational studies of a hybrid cyclic peptide based on cis-β-furanoid sugar amino acid (FSAA) and ornithine
    Chandrasekhar, Srivari
    Saritha, Birudaraju
    Naresh, Police
    Udayakiran, Marelli
    Reddy, Chada Raji
    Jagadeesh, Bharatam
    HELVETICA CHIMICA ACTA, 2008, 91 (07) : 1267 - 1276