Inversion of enantioselectivity in the Diels-Alder synthesis of 2-azabicyclo[2.2.1]hept-5-en-3-one from cyclopentadiene and chiral sulfonyl cyanides

被引：0
作者：
Blanco, JM
Caamano, O
Fernandez, F
GarciaMera, X
Nieto, I
RodriguezBorges, JE
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来源：
HETEROCYCLES | 1997年 / 45卷 / 09期
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中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diels-Alder cycloaddition of (1R,3S,4S)-3-menthanesulfonyl cyanide to cyclopentadiene, followed by treatment with AcOH/H2O, afforded an 11% ee of (+)-(1S)-2-azabicyclo[2.2.1]hept-5-en-3-one [(+)-ent-1]. The analogous process from (1R,3R,4S)-3-menthanesulfonyl cyanide afforded an estimated 12% ee of (-)-1.
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页码：1745 / 1750
页数：6
相关论文
共 17 条
  • [1] SYNTHETIC ANALOGS FOR THE STUDY OF GABA AS A NEUROTRANSMITTER
    ALLAN, RD
    JOHNSTON, GAR
    [J]. MEDICINAL RESEARCH REVIEWS, 1983, 3 (02) : 91 - 118
  • [2] SYNTHESES OF CHIRAL MENTHYL AND NEOMENTHYL SULFIDES, SULFOXIDES AND SULFONES
    BLANCO, JM
    CAAMANO, O
    FERNANDEZ, F
    NIETO, I
    [J]. JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1995, 337 (07): : 538 - 541
  • [3] CHIRAL SULFINIC ACIDS - SYNTHESIS OF SODIUM (1S,2S,5R)-2-ISOPROPYL-5-METHYLCYCLOHEXANESULFINATE BY A NOVEL ROUTE
    BLANCO, JM
    CAAMANO, O
    FERNANDEZ, F
    [J]. TETRAHEDRON, 1995, 51 (03) : 935 - 940
  • [4] A USEFUL SYNTHESIS OF CHIRAL SULFONYL CYANIDES - (1S,2S,5R)-2-ISOPROPYL-5-METHYLCYCLOHEXANESULFONYL CYANIDE
    BLANCO, JM
    CAAMANO, O
    FERNANDEZ, F
    GOMEZ, G
    LOPEZ, C
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (06) : 749 - 752
  • [5] CARBOVIR - THE (-) ENANTIOMER IS A POTENT AND SELECTIVE ANTIVIRAL AGENT AGAINST HUMAN-IMMUNODEFICIENCY-VIRUS INVITRO
    COATES, JAV
    INGGALL, HJ
    PEARSON, BA
    PENN, CR
    STORER, R
    WILLIAMSON, C
    CAMERON, JM
    [J]. ANTIVIRAL RESEARCH, 1991, 15 (02) : 161 - 168
  • [6] CYANOGEN CHLORIDE
    COLEMAN, GH
    LEEPER, RW
    SCHULZE, CC
    [J]. INORGANIC SYNTHESES, 1946, 2 : 90 - 94
  • [7] SYNTHESIS OF CARBOCYCLIC AMINONUCLEOSIDES
    DALUGE, S
    VINCE, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) : 2311 - 2320
  • [8] DIELS-ALDER REACTION OF METHANESULFONYL CYANIDE WITH CYCLOPENTADIENE - INDUSTRIAL SYNTHESIS OF 2-AZABICYCLO[2.2.1]HEPT-5-ENE-3-ONE
    GRIFFITHS, GJ
    PREVIDOLI, FE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) : 6129 - 6131
  • [9] CARBOCYCLIC SUGAR AMINES - SYNTHESIS AND STEREOCHEMISTRY OF RACEMIC ALPHA-CARBOCYCLIC AND BETA-CARBOCYCLIC RIBOFURANOSYLAMINE, CARBOCYCLIC LYXOFURANOSYLAMINE, AND RELATED-COMPOUNDS
    KAM, BL
    OPPENHEIMER, NJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (16) : 3268 - 3272
  • [10] Katagiri N, 1996, CHEM PHARM BULL, V44, P850
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