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Volumn 10, Issue 3, 2012, Pages 502-505

Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS-ACID ACTIVATION; STEREOSPECIFIC MANNER;

EID: 84055178587     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob06776a     Document Type: Article
Times cited : (13)

References (61)
  • 44
    • 0037416957 scopus 로고    scopus 로고
    • 3BH to directly open the protected epoxide 3 but the steric hindrance of the TBS group on the adjacent carbon inhibited the nucleophilic attack of the hydride onto the epoxide Red-Al® (3 equiv.) was also effective, but a lower 56% yield was obtained, maybe due to difficulties in isolating the product from the reaction mixture
    • T. Tachihara T. Kitahara Tetrahedron 2003 59 1773
    • (2003) Tetrahedron , vol.59 , pp. 1773
    • Tachihara, T.1    Kitahara, T.2
  • 50
    • 52649086353 scopus 로고    scopus 로고
    • The relative configuration of compound 7 was deduced from the one of compound 9: removal of the TMS group of the latter led to 7
    • Y. Yamano M. Ito A. Wada Org. Biomol. Chem. 2008 6 3421
    • (2008) Org. Biomol. Chem. , vol.6 , pp. 3421
    • Yamano, Y.1    Ito, M.2    Wada, A.3
  • 54
    • 0032516367 scopus 로고    scopus 로고
    • 2NEt conditions, Jung's group interestingly invoked a Payne rearrangement followed by alkyl migration to explain the formation of a mixture of products from an acyclic α-siloxy epoxide
    • A. Gillmore S. M. Roberts M. B. Hursthouse K. M. Abdul Malik Tetrahedron Lett. 1998 39 3315
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3315
    • Gillmore, A.1    Roberts, S.M.2    Hursthouse, M.B.3    Abdul Malik, K.M.4
  • 55
    • 0004249338 scopus 로고
    • G. Britton and T. W. Goodwin, ed.; Pergamon Press, Oxford, p. 71-86
    • A. Rüttimann, Carotenoid Chemistry and Biochemistry, G. Britton, and, T. W. Goodwin, ed.; Pergamon Press, Oxford, 1982, p. 71-86
    • (1982) Carotenoid Chemistry and Biochemistry
    • Rüttimann, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.