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Volumn , Issue 13, 2005, Pages 1999-2002

Asymmetric desymmetrization of 2-substituted 1,3-propanediols via catalytic enantioselective ring-cleavage reaction of cyclic acetal derivatives

Author keywords

Asymmetric; Catalysis; Cleavage; Diols; Lewis acids

Indexed keywords

3 BENZYLOXY 1 PROPANOL; ACETAL DERIVATIVE; BENZYL DERIVATIVE; LEWIS ACID; OXAZABOROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 23944524914     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871937     Document Type: Article
Times cited : (10)

References (41)
  • 1
    • 33645483731 scopus 로고
    • Morrison, J. D.; Scott, J. W., Eds.; Academic Press: New York
    • (a) Scott, J. W. In Asymmetric Synthesis, Vol. 4; Morrison, J. D.; Scott, J. W., Eds.; Academic Press: New York, 1984, 1.
    • (1984) Asymmetric Synthesis, Vol. 4 , pp. 1
    • Scott, J.W.1
  • 21
    • 0037420342 scopus 로고    scopus 로고
    • For highly enantioselective, catalytic desymmetrization leading to mono-benzyloxy derivatives, see: Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 2410
    • Trost, B.M.1    Mino, T.2
  • 23
    • 0030825714 scopus 로고    scopus 로고
    • For OXB-mediated asymmetric desymmetrization other prochiral polyols, see: (a) Kinugasa, M.; Harada, T.; Oku, A. J. Am. Chem. Soc. 1997, 119, 9067.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9067
    • Kinugasa, M.1    Harada, T.2    Oku, A.3
  • 28
    • 33645495365 scopus 로고    scopus 로고
    • note
    • Acetal 4a was prepared from 2-phenyl-1,3-propanediol and 1-naphthaldehyde (1.1 equiv) under the conventional conditions (p-TsOH, toluene reflux). A pure trans-isomer isolated by recrystallization from EtOAc and hexane (74% yield) was used in ring-cleavage reaction.
  • 29
    • 33645476027 scopus 로고    scopus 로고
    • note
    • For the use of diethyl ether as an additive, see ref. 8 and 9d.
  • 31
    • 33645484629 scopus 로고    scopus 로고
    • note
    • ( 13) The overall enantioselectivity of 6, for example, is calculated by [(syn-6 + anti-6) - (ent-syn-6 + ent-anti-6)}/ {(syn-6 + anti-6) + (ent-syn-6 + ent-anti-6)].
  • 32
    • 33645490152 scopus 로고    scopus 로고
    • note
    • 4 = 46.8 min).
  • 33
    • 0001015876 scopus 로고
    • For the intervention of the silyl ester derivative in asymmetric aldol reaction catalyzed by a relevant OXB, see: Parmee, E. R.; Tempkin, O.; Masamune, S. J. Am. Chem. Soc. 1991, 113, 9365.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9365
    • Parmee, E.R.1    Tempkin, O.2    Masamune, S.3
  • 40
    • 12344335546 scopus 로고    scopus 로고
    • For the use of a dimethylsilyl ketene acetal in OXB-catalyzed asymmetric Michael reaction, see: Harada, T.; Adachi, S.; Wang, X. Org. Lett. 2004, 6, 4877.
    • (2004) Org. Lett. , vol.6 , pp. 4877
    • Harada, T.1    Adachi, S.2    Wang, X.3
  • 41
    • 33645494651 scopus 로고    scopus 로고
    • note
    • 3)}.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.