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Volumn 345, Issue , 2003, Pages 261-267

Zr-catalyzed diastereo- and enantioselective diene cyclizations. An unexpected synthesis of chiral aldehydes

Author keywords

Enantioselective catalysis; Magnesium; Quaternary carbons; Stereoselective synthesis; Zirconocenes

Indexed keywords

ALDEHYDES; CATALYSIS; CYCLIZATION; MAGNESIUM; OLEFINS; STEREOCHEMISTRY; STEREOSELECTIVITY; ZIRCONIUM COMPOUNDS;

EID: 0037430598     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0020-1693(02)01301-4     Document Type: Article
Times cited : (6)

References (37)
  • 1
    • 0001389994 scopus 로고    scopus 로고
    • Zr-catalyzed diastereoselective alkylations: A.H. Hoveyda, Z. Xu, J. Am. Chem. Soc. 113 (1991) 5079.
  • 5
    • 33751386340 scopus 로고
    • Morken J.P., Hoveyda A.H. J. Org. Chem. 58:1993;4237 Zr-catalyzed enantioselective alkylations: J.P. Morken, M.T. Didiuk, A.H. Hoveyda, J. Am. Chem. Soc. 115 (1993) 6697.
    • (1993) J. Org. Chem. , vol.58 , pp. 4237
    • Morken, J.P.1    Hoveyda, A.H.2
  • 6
    • 0001761517 scopus 로고
    • Didiuk M.T., Johannes C.W., Morken J.P., Hoveyda A.H. J. Am. Chem. Soc. 117:1995;7097 Zr-catalyzed kinetic resolution through enantioselective alkylation: J.P. Morken, M.T. Didiuk, M.S. Visser, A.H. Hoveyda, J. Am. Chem. Soc. 116 (1994) 3123.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 7097
    • Didiuk, M.T.1    Johannes, C.W.2    Morken, J.P.3    Hoveyda, A.H.4
  • 29
    • 0013360902 scopus 로고    scopus 로고
    • For a review on enantioselective synthesis of quaternary carbon centers, see: E.J. Corey, A. Guzman-Perez, Angew. Chem. Int. Ed. 37 (1998) 388 For a recent related example from these laboratories, see: C.A. Luchaco-Cullis, H. Mizutani, K.E. Murphy, A.H. Hoveyda Angew. Chem. Int. Ed. 40 (2001) 1456.
  • 30
    • 0013413280 scopus 로고    scopus 로고
    • note
    • The methyl ether derived from 4 efficiently undergoes Zr-catalyzed cyclization but with significantly lower level of diastereoselectivity (6-8:1 by GLC analysis). It should be noted that in the absence of the quaternary carbon site within the acyclic chain, <5% conversion is observed under identical conditions.
  • 32
    • 11744317080 scopus 로고    scopus 로고
    • For key disclosures on β-Zr-hydride elimination, see: S.L. Buchwald, R.B. Nielsen, Chem. Rev. 88 (1988) 1047.
  • 37
    • 0013415434 scopus 로고    scopus 로고
    • note
    • In spite of extensive attempts we have not yet been able to determine the identity of the major enantiomers formed in the reactions shown in Table 2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.