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Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes.

ABSTRACT: A catalytic, enantio-, and diastereoselective formation of sulfenyl acetals bearing multiple stereogenic centers is reported. Alkenyl aldehydes undergo a chiral thiiranium ion initiated cascade starting with intramolecular capture by a formyl group and termination by capture with HFIP solvent. This method provides a one-pot synthesis of dihydropyran and 1,3-disubstituted isochroman acetals in good to excellent yield and with high levels of diastereo- (up to >99:1 dr) and enantiocontrol (up to 99:1 er).

SUBMITTER: Matviitsuk A

PROVIDER: S-EPMC6713611 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes.

Matviitsuk Anastassia A Denmark Scott E SE

Angewandte Chemie (International ed. in English) 20190801 36

A catalytic, enantio-, and diastereoselective formation of sulfenyl acetals bearing multiple stereogenic centers is reported. Alkenyl aldehydes undergo a chiral thiiranium ion initiated cascade starting with intramolecular capture by a formyl group and termination by capture with HFIP solvent. This method provides a one-pot synthesis of dihydropyran and 1,3-disubstituted isochroman acetals in good to excellent yield and with high levels of diastereo- (up to >99:1 dr) and enantiocontrol (up to 99 ...[more]

PMID: 31295383

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