Controlled Heterocyclization/Cross‐Coupling Domino Reaction of β,γ‐Allendiols and α‐Allenic Esters: Method and Mechanistic Insight for the Preparation of Functionalized Buta‐1,3‐dienyl Dihydropyrans | Zendy

Alcaide Benito | Zendy; Almendros Pedro | Zendy; Martínez del Campo Teresa | Zendy; Quirós M. Teresa | Zendy; Soriano Elena | Zendy; MarcoContelles José L. | Zendy

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Controlled Heterocyclization/Cross‐Coupling Domino Reaction of β,γ‐Allendiols and α‐Allenic Esters: Method and Mechanistic Insight for the Preparation of Functionalized Buta‐1,3‐dienyl Dihydropyrans

Author(s) -

Alcaide Benito,

Almendros Pedro,

Martínez del Campo Teresa,

Quirós M. Teresa,

Soriano Elena,

MarcoContelles José L.

Publication year - 2013

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201300774

Subject(s) - enantiopure drug , moiety , domino , chemistry , coupling reaction , coupling (piping) , combinatorial chemistry , palladium , organic chemistry , computational chemistry , catalysis , enantioselective synthesis , materials science , metallurgy

Starting from β,γ‐allendiols and α‐allenic acetates, a chemo‐ and regiocontrolled palladium‐catalyzed methodology has provided access to enantiopure 3,6‐dihydropyrans that bear a buta‐1,3‐dienyl moiety. Thus, it has been demonstrated for the first time that the preparation of six‐membered heterocycles through cross‐coupling reactions of two different allenes can be accomplished. These heterocyclization/cross‐coupling reactions have been developed experimentally and their mechanisms have additionally been investigated by a computational study.

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