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Volumn 36, Issue 16, 1997, Pages 1764-1766

Synthesis of Enantiomerically and Diastereomerically Pure Cyclopentanols by Asymmetric Cyclocarbolithiation of 5-Alkenyl Carbamates

Author keywords

( ) sparteine; Asymmetric synthesis; Carbanions; Carbolithiations; Cyclopentanols

Indexed keywords


EID: 0030827702     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199717641     Document Type: Article
Times cited : (64)

References (33)
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    • (1993) Methoden Org. Chem. (Houben-Weyl), 4th Ed. 1952 , vol.E19D , pp. 744-754
    • Subramanian, R.L.1
  • 2
    • 0001522634 scopus 로고
    • Eds.: B. M. Trost, I. Fleming, Pergamon, New York
    • Reviews: a) R. L. Subramanian, Methoden Org. Chem. (Houben-Weyl), 4th ed. 1952-, Vol. E19d, 1993, pp. 744-754; b) P. Knochel in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 865; c) J.-F. Normant, Chemtracts: Org. Chem. 1994, 7, 59-73.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 865
    • Knochel, P.1
  • 3
    • 0002449911 scopus 로고
    • Reviews: a) R. L. Subramanian, Methoden Org. Chem. (Houben-Weyl), 4th ed. 1952-, Vol. E19d, 1993, pp. 744-754; b) P. Knochel in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 865; c) J.-F. Normant, Chemtracts: Org. Chem. 1994, 7, 59-73.
    • (1994) Chemtracts: Org. Chem. , vol.7 , pp. 59-73
    • Normant, J.-F.1
  • 5
    • 84912964962 scopus 로고
    • a) V. N. Drozd, U. A. Ustynyuk, M. A. Tsel'eva, L. B. Dmitriev, J. Gen. Chem. USSR 1968, 38, 2047; Zh. Obsch. Khan. 1968, 38, 2144;
    • (1968) Zh. Obsch. Khan. , vol.38 , pp. 2144
  • 7
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    • and references therein
    • c) W. F. Bailey, K. V. Gavaskar, Tetrahedron 1994, 50, 5957-5970, and references therein;
    • (1994) Tetrahedron , vol.50 , pp. 5957-5970
    • Bailey, W.F.1    Gavaskar, K.V.2
  • 8
    • 0007884867 scopus 로고    scopus 로고
    • and references therein
    • d) A. Krief, J. Bousbaa, Synlett 1996, 1007-1009, and references therein.
    • (1996) Synlett , pp. 1007-1009
    • Krief, A.1    Bousbaa, J.2
  • 11
    • 0343583098 scopus 로고
    • a) D. Hoppe, F. Hintze. P. Tebben, Angew. Chem. 1990, 102, 1457-1459; Angew. Chem. Int. Ed. Eng. 1990, 29, 1422-1423;
    • (1990) Angew. Chem. Int. Ed. Eng. , vol.29 , pp. 1422-1423
  • 13
    • 0642329707 scopus 로고    scopus 로고
    • note
    • 2O, reflux, 1 h, then aldehyde (6), RT. 15 h, 1b: 81% (Z:E = 46:54).
  • 15
    • 0642299137 scopus 로고    scopus 로고
    • note
    • 3Si (465.709): C 72.21, H 8.44, N 3.01; found: C 72.29, H 8.49, N 3.26.
  • 16
    • 0642329708 scopus 로고    scopus 로고
    • note
    • The crude carboxylic acid was converted into the methyl ester 5g by treatment with diazomethane. A small amount of the carboxylate presumably epimerizes under the work-up conditions.
  • 17
    • 0642329711 scopus 로고    scopus 로고
    • note
    • 3 to be greater than 95%.
  • 18
    • 0642299138 scopus 로고    scopus 로고
    • note
    • The by-products of the reactions of la were the corresponding open-chain substitution product and the cyclopropane derivative resulting from intramolecular 1,3-elimination of the carbamate group. Reactions of 1b delivered the cyclopropane derivative as well as the substrate. Therefore, in case of 1a the yields are limited either by the rate of cyclization or the unfavorable equilibrium constant, whereas for 1b the slow deprotonation step plays a crucial role. Other by-products were not identified.
  • 20
    • 0642360407 scopus 로고    scopus 로고
    • note
    • D = -46.8 (c = 1.10 in MeOH)[11]).
  • 26
    • 0642268451 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100 367. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: int. code +(1223)336-033; e-mail; deposit@chemcrys.cam.ac.uk).
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    • 0343177680 scopus 로고
    • a) D. Hoppe, A. Carstens, T. Krämer, Angew. Chem. 1990, 102, 1455-1456; Angew. Chem. Int. Ed. Eng. 1990, 29, 1424-1425;
    • (1990) Angew. Chem. Int. Ed. Eng. , vol.29 , pp. 1424-1425
  • 30
    • 0642268450 scopus 로고    scopus 로고
    • note
    • However, protonations occur under retention of configuration [15,17]. Therefore, for E1 = H the other benzylic epimer must be generated. As this is not of any significance for the examples described in here, the structure of 1′-epi-5 is not shown.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.