Activated cyclooctenones are effective dienophiles | Zendy

HsingJang Liu | Zendy; Dan-Xiong Wang | Zendy; Jeung Bea Kim | Zendy; E. N. C. BROWNE | Zendy; Yu Wang | Zendy

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Activated cyclooctenones are effective dienophiles

Author(s) -

HsingJang Liu,

Dan-Xiong Wang,

Jeung Bea Kim,

E. N. C. BROWNE,

Yu Wang

Publication year - 1997

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v97-108

Subject(s) - chemistry , diene , stereoselectivity , adduct , lewis acids and bases , selectivity , ring (chemistry) , diels–alder reaction , catalysis , organic chemistry , stereochemistry , medicinal chemistry , natural rubber

The first Diels–Alder addition of a diene to a cyclooctenone dienophile has been observed. Three activated cyclooctenone dienophiles 1, 2, and 3 are studied with a variety of simple and functionalized dienes. Diels–Alder adducts are produced in excellent yields under very mild Lewis acid catalyzed conditions. The usual orientation rules are followed and, as predicted, the products are formed for the most part exclusively by ester-endo addition. The stereoselectivity is influenced by the substitution pattern of the diene in some cases. The factors influencing the stereochemical selectivity of the addition are discussed in some detail. Keywords: 2-carbalkoxy-2-cyclooctenones, Diels–Alder reaction, six–eight fused ring system.

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