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Volumn 43, Issue 25, 2004, Pages 3258-3260

Highly diastereo- and enantioselective reactions of enecarbamates with ethyl glyoxylate to give optically active syn and anti α-alkyl-β- hydroxy imines and ketones

Author keywords

Asymmetric catalysis; Aza ene reaction; Copper N ligands; Synthetic methods

Indexed keywords

CATALYSTS; COPPER; REACTION KINETICS; STEREOCHEMISTRY;

EID: 4544373680     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460165     Document Type: Article
Times cited : (67)

References (37)
  • 2
    • 0000487061 scopus 로고
    • (Ed.: B. M. Trost), Pergamon, Oxford
    • Reviews: a) C. H. Heathcock in Comprehensive Organic Synthesis, Vol. 2 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, p. 181;
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 181
    • Heathcock, C.H.1
  • 4
    • 0003913629 scopus 로고    scopus 로고
    • (Ed.: J. Otera), Wiley-VCH, Weinheim
    • c) E. M. Carreira in Modern Carbonyl Chemistry (Ed.: J. Otera), Wiley-VCH, Weinheim, 2000, p. 227.
    • (2000) Modern Carbonyl Chemistry , pp. 227
    • Carreira, E.M.1
  • 7
    • 0001702357 scopus 로고    scopus 로고
    • (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin
    • E. M. Carreira in Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 998.
    • (1999) Comprehensive Asymmetric Catalysis , pp. 998
    • Carreira, E.M.1
  • 9
    • 4544283548 scopus 로고    scopus 로고
    • R. Matsubara, Y. Nakamura, S. Kobayashi, Angew. Chem. 2004, 116, 1711; Angew. Chem. Int. Ed. 2004, 43, 1679.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1679
  • 22
    • 4544246946 scopus 로고    scopus 로고
    • note
    • Enecarbamates are readily prepared (see Supporting Information).
  • 23
    • 0034714254 scopus 로고    scopus 로고
    • The absolute configuration of 5a was determined by the comparison of HPLC retention time: P. Herold, A. F. Indolese, M. Studer, H. P. Jalett, U. Siegrist, H. U. Blaser, Tetrahedron 2000, 56, 6497; the absolute configuration of 5f was also determined by the Mosher esterification method (see Supporting Information).
    • (2000) Tetrahedron , vol.56 , pp. 6497
    • Herold, P.1    Indolese, A.F.2    Studer, M.3    Jalett, H.P.4    Siegrist, U.5    Blaser, H.U.6
  • 26
    • 1542586711 scopus 로고
    • For Mukaiyama-type catalytic asymmetric aldol reactions of glyoxylates, see: a) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1993, 115, 7039;
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 7039
    • Mikami, K.1    Matsukawa, S.2
  • 33
    • 4544286731 scopus 로고    scopus 로고
    • See also Supporting Information
    • See also Supporting Information.
  • 37
    • 4544253429 scopus 로고    scopus 로고
    • note
    • The reactions with imines did not proceed stereospecifically; see reference [5].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.