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Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes.

ABSTRACT: We report the development of a multicatalytic, one-pot, asymmetric Michael/Stetter reaction between salicylaldehydes and electron-deficient alkynes. The cascade proceeds via amine-mediated Michael addition followed by an N-heterocyclic carbene-promoted intramolecular Stetter reaction. A variety of salicylaldehydes, doubly activated alkynes, and terminal, electrophilic allenes participate in a one-step or two-step protocol to give a variety of benzofuranone products in moderate to good yields and good to excellent enantioselectivities. The origin of enantioselectivity in the reaction is also explored; E/Z geometry of the reaction intermediate as well as the presence of catalytic amounts of catechol additive are found to influence reaction enantioselectivity.

SUBMITTER: Filloux CM

PROVIDER: S-EPMC2996425 | biostudies-other | 2010 Nov

REPOSITORIES: biostudies-other

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Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes.

Filloux Claire M CM Lathrop Stephen P SP Rovis Tomislav T

Proceedings of the National Academy of Sciences of the United States of America 20100716 48

We report the development of a multicatalytic, one-pot, asymmetric Michael/Stetter reaction between salicylaldehydes and electron-deficient alkynes. The cascade proceeds via amine-mediated Michael addition followed by an N-heterocyclic carbene-promoted intramolecular Stetter reaction. A variety of salicylaldehydes, doubly activated alkynes, and terminal, electrophilic allenes participate in a one-step or two-step protocol to give a variety of benzofuranone products in moderate to good yields and ...[more]

PMID: 20639467

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