Annulation Reactions of Allenyl Esters: An Approach to Bicyclic Diones and Medium-Sized Rings | Zendy

Bilal A. Bhat | Zendy; S. Maki | Zendy; Elijah J. St.Germain | Zendy; Pradip Maity | Zendy; Salvatore D. Lepore | Zendy

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Annulation Reactions of Allenyl Esters: An Approach to Bicyclic Diones and Medium-Sized Rings

Author(s) -

Bilal A. Bhat,

S. Maki,

Elijah J. St.Germain,

Pradip Maity,

Salvatore D. Lepore

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo501700c

Subject(s) - bicyclic molecule , chemistry , aldol reaction , annulation , steric effects , intramolecular force , lactone , intramolecular reaction , potassium carbonate , medicinal chemistry , stereochemistry , organic chemistry , catalysis

A flexible approach to construct sterically congested bicyclo-alkenedione frameworks is reported. Under the action of potassium carbonate, α-sulphonyl cycloalkanones are added to functionalized allenyl esters, leading to a lactone intermediate that is subsequently reduced to initiate an intramolecular aldol cyclization to [3.2.1], [3.3.1], and [4.3.1] bicycles. Oxidation then affords bicyclic diones in good three-step yields. Under exceptionally mild conditions, these bicycles are converted to highly functionalized medium-sized rings through a Grob-type fragmentation.

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