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Volumn 7, Issue 24, 2005, Pages 5429-5431

Room temperature intramolecular hydro-O-alkylation of aldehydes: sp 3 C-H functionalization via a lewis acid catalyzed tandem 1,5-hydride transfer/cyclization

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

EID: 28844500714     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0522283     Document Type: Article
Times cited : (138)

References (16)
  • 4
    • 0037307278 scopus 로고    scopus 로고
    • For reviews on the synthesis of spiroketals including spirioketal natural products, see: (a) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227-256.
    • (2003) Curr. Org. Chem. , vol.7 , pp. 227-256
    • Mead, K.T.1    Brewer, B.N.2
  • 7
  • 10
    • 28844482990 scopus 로고    scopus 로고
    • note
    • 4.
  • 11
    • 0343485820 scopus 로고
    • For deuterium studies regarding the epimerization of spirostanols, see: Seo, S.; Uomori, A.; Takeda, K. J. Org. Chem. 1986, 51, 3823-3827.
    • (1986) J. Org. Chem. , vol.51 , pp. 3823-3827
    • Seo, S.1    Uomori, A.2    Takeda, K.3
  • 12
    • 28844452012 scopus 로고    scopus 로고
    • See Supporting Information for details
    • DFT calculations were preformed using Jaguar 4.1. See Supporting Information for details.
  • 13
    • 28844444663 scopus 로고    scopus 로고
    • note
    • Subjection of 21 to the reaction conditions yields the same ratio of 20:21.
  • 14
    • 28844462497 scopus 로고    scopus 로고
    • note
    • The formation of 21 from 20 is essentially the reverse of the reactions in ref 4.
  • 15
    • 28844451204 scopus 로고
    • The opening of a spiroketal without substitution along the tether has been reported: Deslongchamps, P.; Rowan, D. D.; Potheir, N. Heterocycles 1981, 15, 1093-1096.
    • (1981) Heterocycles , vol.15 , pp. 1093-1096
    • Deslongchamps, P.1    Rowan, D.D.2    Potheir, N.3
  • 16
    • 28844501836 scopus 로고    scopus 로고
    • note
    • Aldol products were found to be the major products of these reactions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.