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Asymmetric Organocatalytic Sulfa-Michael Addition to Enone Diesters.

ABSTRACT: An asymmetric sulfa-Michael addition of alkyl thiols to enone diesters is reported. The reaction is catalyzed by a bifunctional triaryliminophosphorane-thiourea organocatalyst and provides a range of ?-sulfaketones in high yields and enantioselectivities. Leveraging the gem-diester functional handle via a subsequent diastereotopic group discrimination generates functionalized lactones with three contiguous stereocenters.

SUBMITTER: Fulton JL

PROVIDER: S-EPMC5856655 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Asymmetric Organocatalytic Sulfa-Michael Addition to Enone Diesters.

Fulton Jennifer L JL Horwitz Matthew A MA Bruske Ericka L EL Johnson Jeffrey S JS

The Journal of organic chemistry 20180307 6

An asymmetric sulfa-Michael addition of alkyl thiols to enone diesters is reported. The reaction is catalyzed by a bifunctional triaryliminophosphorane-thiourea organocatalyst and provides a range of α-sulfaketones in high yields and enantioselectivities. Leveraging the gem-diester functional handle via a subsequent diastereotopic group discrimination generates functionalized lactones with three contiguous stereocenters. ...[more]

PMID: 29512387

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