Tandem conjugate addition–aldol cyclization of 2-formylbenzylidenemalonate with ether radicals by the mediation of dimethylzinc

The chemoselective radical conjugate addition reaction of THF or 4,4,5,5-tetramethyl-1,3-dioxolane with 2-formylbenzylidenemalonate gave tandem conjugate addition–aldol cyclization product in one pot. The radical tandem reaction was extended to the asymmetric reaction using bis(8-phenylmenthyl) 2-fo...

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Bibliographic Details
Published in:Tetrahedron 2009-01, Vol.65 (4), p.903-908
Main Authors: Yamada, Ken-ichi, Maekawa, Masaru, Akindele, Tito, Yamamoto, Yasutomo, Nakano, Mayu, Tomioka, Kiyoshi
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Free radicals chemistry
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Summary:The chemoselective radical conjugate addition reaction of THF or 4,4,5,5-tetramethyl-1,3-dioxolane with 2-formylbenzylidenemalonate gave tandem conjugate addition–aldol cyclization product in one pot. The radical tandem reaction was extended to the asymmetric reaction using bis(8-phenylmenthyl) 2-formylbenzylidenemalonate as a chiral Michael acceptor to provide an enantioenriched indane derivative. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.11.009