Efficient syntheses of four stable-isotope labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylates

被引：10
|
作者：
Keliher, Edmund J. [1 ]
Burrell, Richard C. [1 ]
Chobanian, Harry R. [1 ]
Conkrite, Karina L. [1 ]
Shukla, Rajesh [1 ]
Baldwin, John E. [1 ]
机构：
[1] Syracuse Univ, Dept Chem, Syracuse, NY 13244 USA
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 14期
关键词：
D O I：
10.1039/b605912k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Many carbenoid cyclopropanation reactions promoted by chiral catalysts give product mixtures reflecting impressive diastereo- and enantioselectivities. Few provide a single chiral product efficiently. This limitation has been overcome in cyclopropanations of styrene and isotopically labeled styrenes with alpha-diazoacetates. Convenient syntheses on a 20 g scale of each of four chiral isotopically labeled (1R)-menthyl(1S, 2S)-2-phenylcyclopropanecarboxylates ( the 1-d- 3-C-13,1,(3S)-d(2), 1,2,( 3S)-d(3), and 1,3,3-d(3) isotopomers) of better than 99% ee have been realized.
引用
收藏
页码：2777 / 2784
页数：8
相关论文
共 50 条
  • [1] ENANTIOSELECTIVE SYNTHESIS OF (1R,2S) AND (1S,2S) DEHYDROCORONAMIC ACIDS
    FLICHE, C
    BRAUN, J
    LEGOFFIC, F
    SYNTHETIC COMMUNICATIONS, 1994, 24 (20) : 2873 - 2876
  • [2] Studies towards the synthesis of (1R,2S)- and (1S,2S)-1,2-epoxy-3-hydroxypropylphosphonates and (1S, 2S)- and (1R,2S)-2,3-epoxy-1-hydroxypropylphosphonates
    Wroblewski, Andrzej E.
    Bak-Sypien, Irena I.
    TETRAHEDRON-ASYMMETRY, 2007, 18 (18) : 2218 - 2226
  • [3] Synthesis of novel 1,3,4-oxadiazinane-2-thiones derived from (1R,2S)-ephedrine, (1S,2S)-pseudoephedrine and (1R,2S)-norephedrine
    Hitchcock, SR
    Nora, GP
    Casper, DM
    Wiman, JD
    Bentley, JT
    Stafford, C
    Squire, MD
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (05) : 1113 - 1115
  • [4] Synthesis of (1R,2S)- and (1S,2S)-3-azido-1,2-dihydroxypropylphosphonates
    Wróblewski, AE
    Glowacka, IE
    TETRAHEDRON-ASYMMETRY, 2002, 13 (09) : 989 - 994
  • [5] (1R,2S,5R)-menthyl phosphinate and its properties
    Kolodyazhnyi, OI
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2005, 75 (04) : 656 - 657
  • [6] Enantioselective synthesis of (1R,2R)- and (1S,2S)-2-nitroxycyclohexan-1-ols
    Basavaiah, D
    Pandiaraju, S
    Muthukumaran, K
    TETRAHEDRON-ASYMMETRY, 1996, 7 (01) : 13 - 16
  • [7] Synthesis of (+)-(1S,2R) and (-)-(1R,2S)-2-aminocyclobutane-1-carboxylic acids
    Gauzy, C
    Pereira, E
    Faure, S
    Aitken, DJ
    TETRAHEDRON LETTERS, 2004, 45 (38) : 7095 - 7097
  • [8] An easy entry to (1S, 2S) and (1R, 2R)-threo-ifenprodil
    Mantegani, S
    Arlandini, E
    Brambilla, E
    Cremonesi, P
    Varasi, M
    SYNTHETIC COMMUNICATIONS, 2000, 30 (19) : 3543 - 3553
  • [9] Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols
    Kolodiazhna, Olga O.
    Kolodiazhna, Anastasy O.
    Kolodiazhnyi, Oleg I.
    TETRAHEDRON-ASYMMETRY, 2013, 24 (01) : 37 - 42
  • [10] Synthesis of (1S,2S)- and (1R,2S)-3-amino-1,2-dihydroxypropylphosphonic acids
    Wróblewski, AE
    Glowacka, IE
    POLISH JOURNAL OF CHEMISTRY, 2005, 79 (12) : 1895 - 1899
12345