Allenyldiene electrocyclization. A stereospecific tandem center-axis-center chirality transfer: Synthesis of drimatrienes and related trans-decalins

Journal of the American Chemical Society

Volumn 107, Issue 4, 1985, Pages 1034-1041

  Okamura, William H ^a   Peter, Roland ^a   Reischl, Wolfgang ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845377977     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00290a047     Document Type: Article

References (44)

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22. 4-Chirald. Neat Alpine-borane (see: Brown, H. C.; Pai, G. G. J. Org. Chem. 1982, 47, 1606) afforded R-15 in 73% ee (56% yield) using 92% ee α-pinene.
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28. MoOPH refers to the 1:1:1 complex of molybdenum pentoxide, pyridine, and hexamethylphosphoramide. See: Little, R. D.; Myong, S. O. Tetrahedron Lett. 1980, 21, 3339. Vedejs, E.; Engler, D. A.; Telschow, J. E. J. Org. Chem. 1978, 43, 188.
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40. 1 π-bond of the allene moiety. However, Pasto has examined the (2 + 2) cycloaddition of allenes and olefins in terms of a stereoselective process where all three πsystems participate in a concerted fashion. See Pasto, D. J. J. Am. Chem. Soc. 1979, 101, 37.
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43. We are grateful to Prof. Robert K. Boeckman for this interesting suggestion. For leading references on neighboring charge accelerated pericyclic processes, see: Evans, D. A.; Golob, A. M. J. Am. Chem. Soc. 1975, 97, 4765. Carpenter, B. K. Tetrahedron 1978, 34, 1877.
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