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Volumn 47, Issue 8, 2008, Pages 1450-1453

Amine-catalyzed cyclizations of tethered α,β-unsaturated carbonyl compounds

Author keywords

Aldehydes; Cyclization; Diels Alder reactions; Michael addition; Organocatalysis

Indexed keywords

AMINES; CARBONYLATION; CHEMICAL COMPOUNDS; CHEMICAL REACTIONS; ORGANIC COMPOUNDS;

EID: 48349119169     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704688     Document Type: Article
Times cited : (130)

References (91)
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    • C. Starkenmann, F. Mayenzet, R. Brauchi, L. Wunsche, C. Vial, Agric. Food Chem. 2007, 55, 10902. While this manuscript was in production, we became aware of Hong's independent investigations (reference [8d]) on the cyclizations of compounds 5a and 5b. The products 8a and 8b were suggested to be the thermodynamically more stable cis diastereomer. Very recently, (±)-8a was identified as a pungent constituent of black cardamom (reference [8d]). Independent analyses by NMR spectroscopy (Starkmann et al.) and X-ray crystallography (this work) confirm that amine-catalyzed cyclizations favor the trans diastereomer.
    • e) C. Starkenmann, F. Mayenzet, R. Brauchi, L. Wunsche, C. Vial, Agric. Food Chem. 2007, 55, 10902. While this manuscript was in production, we became aware of Hong's independent investigations (reference [8d]) on the cyclizations of compounds 5a and 5b. The products 8a and 8b were suggested to be the thermodynamically more stable cis diastereomer. Very recently, (±)-8a was identified as a pungent constituent of black cardamom (reference [8d]). Independent analyses by NMR spectroscopy (Starkmann et al.) and X-ray crystallography (this work) confirm that amine-catalyzed cyclizations favor the trans diastereomer.
  • 25
    • 55049138759 scopus 로고    scopus 로고
    • Ed, P. I. Dalko, Wiley-VCH, Weinheim
    • b)Enantioselective Organocatalysis (Ed.: P. I. Dalko), Wiley-VCH, Weinheim, 2007.
    • (2007) Enantioselective Organocatalysis
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  • 40
    • 34250669449 scopus 로고    scopus 로고
    • For a review, see: c
    • For a review, see: c) C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042;
    • (2006) Angew. Chem , vol.118 , pp. 8042
    • Palomo, C.1    Mielgo, A.2
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    • 1d was prepared by modification of J. V. Bhaskar Kanth, M. Periasamy, Tetrahedron 1993, 49, 5127. PhMgBr was substituted by a mixed Grignard reagent prepared from a 1:1 mixture of two aryl bromides. Along with N-protected 1a (major product), the precursor of 1d was obtained in 31% yield. Our rationale involves initial addition of PhMgBr and subsequent chelation controlled addition of the other ArMgBr species. (Chemical Equation Presented)
    • 1d was prepared by modification of J. V. Bhaskar Kanth, M. Periasamy, Tetrahedron 1993, 49, 5127. PhMgBr was substituted by a mixed Grignard reagent prepared from a 1:1 mixture of two aryl bromides. Along with N-protected 1a (major product), the precursor of 1d was obtained in 31% yield. Our rationale involves initial addition of PhMgBr and subsequent chelation controlled addition of the other ArMgBr species. (Chemical Equation Presented)
  • 72
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    • List and co-workers encountered similar problems in enolexo aldolizations: C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2891;
    • List and co-workers encountered similar problems in enolexo aldolizations: C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2891;
  • 91
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    • For 1,4-additions of organocuprates to bicylic 2,4-dienals in natural product synthesis, see
    • For 1,4-additions of organocuprates to bicylic 2,4-dienals in natural product synthesis, see: J. A. Marshall, J. E. Audia, B. G. Shearer, J. Org. Chem. 1986, 51, 1730.
    • (1986) J. Org. Chem , vol.51 , pp. 1730
    • Marshall, J.A.1    Audia, J.E.2    Shearer, B.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.