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Brønsted Acid‐Catalyzed, Highly Enantioselective Addition of Enamides to In Situ ‐ Generated ortho ‐Quinone Methides: A Domino Approach to Complex Acetamidotetrahydroxanthenes
Author(s) -
Saha Satyajit,
Schneider Christoph
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406044
Subject(s) - enantioselective synthesis , in situ , phosphoric acid , catalysis , domino , chemistry , brønsted–lowry acid–base theory , conjugate , quinone , xanthene , organic chemistry , combinatorial chemistry , mathematical analysis , mathematics
Abstract The highly enantioselective conjugate addition of enamides and enecarbamates to in situ‐generated ortho ‐quinone methides, upon subsequent N,O‐acetalization, gives rise to acetamido‐substituted tetrahydroxanthenes with generally excellent enantio‐ and diastereoselectivities. A chiral BINOL‐based phosphoric acid catalyst controls the enantioselectivity of the carbon–carbon bond‐forming event. The products are readily converted into other xanthene‐based heterocycles.