Asymmetric Auto-Tandem Catalysis with Chiral Organosuperbases: Intramolecular Cyclization/Enantioselective Direct Mannich-Type Addition Sequence

An enantioselective addition reaction of alkynyl esters with imines was developed under asymmetric autotandem catalysis with a chiral Brønsted base. A chiral bis­(guanidino)­iminophosphorane organosuperbase, which has much higher basicity than that of conventional chiral organic bases, efficiently p...

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Bibliographic Details
Published in:Organic letters 2024-08, Vol.26 (30), p.6523-6528
Main Authors: Kondoh, Azusa, Kato, Takuro, Chen, Hao, Terada, Masahiro
Format: Article
Language:English
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Summary:An enantioselective addition reaction of alkynyl esters with imines was developed under asymmetric autotandem catalysis with a chiral Brønsted base. A chiral bis­(guanidino)­iminophosphorane organosuperbase, which has much higher basicity than that of conventional chiral organic bases, efficiently promoted both the intramolecular cyclization for the construction of a benzofuran ring or a benzothiophene ring and the sequential enantioselective direct Mannich-type reaction of diarylmethane derivatives, affording enantio-enriched diarylalkane derivatives that are otherwise difficult to access.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02532