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Volumn 71, Issue 25, 2006, Pages 9519-9521

Enantioselective synthesis of γ-aryl-γ-butyrolactones by sequential asymmetric epoxidation, ring expansion, and Baeyer-Villiger oxidation

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHEMICAL MODIFICATION; KETONES;

EID: 33845534717     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061341j     Document Type: Article
Times cited : (51)

References (42)
  • 1
    • 0000439864 scopus 로고
    • For examples on the synthesis of optically active γ-butyrolactones, see: (a) Gutman, A. L.; Zuobi, K.; Bravdo, T. J. Org. Chem. 1990, 55, 3546.
    • (1990) J. Org. Chem. , vol.55 , pp. 3546
    • Gutman, A.L.1    Zuobi, K.2    Bravdo, T.3
  • 13
    • 33745289056 scopus 로고
    • For leading references on the rearrangement of oxaspiropentanes and oxaspirohexanes, see: (a) Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1972, 94, 4777.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 4777
    • Trost, B.M.1    Bogdanowicz, M.J.2
  • 22
    • 0001077163 scopus 로고    scopus 로고
    • For leading references on asymmetric dihydroxylation of cyclopropylidene derivatives and subsequent rearrangement, see: (a) Krief, A.; Ronvaux, A.; Tuch, A. Bull. Soc. Chim. Belg. 1997, 106, 699.
    • (1997) Bull. Soc. Chim. Belg. , vol.106 , pp. 699
    • Krief, A.1    Ronvaux, A.2    Tuch, A.3
  • 35
    • 33745289112 scopus 로고    scopus 로고
    • For asymmetric epoxidation of trisubstituted and tetrasubstituted benzylidenecyclobutane derivatives with ketone 6, see: (a) Shen, Y.-M.; Wang, B.; Shi, Y. Angew. Chem., Int. Ed. 2006, 45, 1429.
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 1429
    • Shen, Y.-M.1    Wang, B.2    Shi, Y.3
  • 37
    • 33845525880 scopus 로고    scopus 로고
    • note
    • For the synthesis of ketone 6 see: (a) ref. 8a.
  • 39
    • 33845528210 scopus 로고    scopus 로고
    • note
    • The enantioselectivity was determined by chiral GC (chiraldex B-DM). The absolute configuration of 2-methyl-2-tolylcyclobutanone was determined by comparing the measured optical rotation with the reported one (ref 4a). The absolute configuration of 2-(p-tert-butylphenyl)cyclobutanone was tentatively assigned based on mechanistic considerations.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.