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Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis.

ABSTRACT: We report herein an efficient synthesis of furopyran derivatives through a gold(I)-catalyzed domino reaction. The cascade reaction starts with two regioselective cyclizations, a 5-endo-dig and a 8-endo-dig, followed with a Grob-type fragmentation and a hetero Diels-Alder. The obtained furopyran derivatives contain fused and spiro-heterocycles. During this one-pot process, four bonds and four controlled stereogenic centers including a quaternary center are formed.

SUBMITTER: Ruch M

PROVIDER: S-EPMC7663467 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis.

Ruch Marie M Brach Nicolas N Galéa Roméric R Wagner Patrick P Blond Gaëlle G

Molecules (Basel, Switzerland) 20201027 21

We report herein an efficient synthesis of furopyran derivatives through a gold(I)-catalyzed domino reaction. The cascade reaction starts with two regioselective cyclizations, a 5-<i>endo</i>-dig and a 8-<i>endo</i>-dig, followed with a Grob-type fragmentation and a hetero Diels-Alder. The obtained furopyran derivatives contain fused and spiro-heterocycles. During this one-pot process, four bonds and four controlled stereogenic centers including a quaternary center are formed. ...[more]

PMID: 33121149

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