Selectivities in Chiral Lewis Acid Catalyzed Diels–Alder Reactions of Acetylenic Ketones: Explanation for Differences of Selectivities between Acylic and Cyclic Dienes | Zendy

Payette Joshua N. | Zendy; Akakura Matsujiro | Zendy; Yamamoto Hisashi | Zendy

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Selectivities in Chiral Lewis Acid Catalyzed Diels–Alder Reactions of Acetylenic Ketones: Explanation for Differences of Selectivities between Acylic and Cyclic Dienes

Author(s) -

Payette Joshua N.,

Akakura Matsujiro,

Yamamoto Hisashi

Publication year - 2011

Publication title -

chemistry – an asian journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.18

H-Index - 106

eISSN - 1861-471X

pISSN - 1861-4728

DOI - 10.1002/asia.201000687

Subject(s) - cationic polymerization , chemistry , lewis acids and bases , catalysis , organic chemistry , diels–alder reaction , medicinal chemistry , computational chemistry

Huey Lewis (acid) and the News : Crystallographic and computational studies on the cationic‐oxazaborolidine‐catalyzed Diels–Alder reaction of acetylenic ketones indicated that the reaction proceeds through a favored syn, exo transition state. These results provide a basis for understanding why acyclic dienes give higher enantioselectivities than cyclic dienes.

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