TY - JOUR T1 - Brønsted acid-catalyzed, highly enantioselective addition of enamides to in situ-generated ortho-quinone methides: a domino approach to complex acetamidotetrahydroxanthenes. AU - Saha,Satyajit, AU - Schneider,Christoph, Y1 - 2014/12/08/ PY - 2014/08/13/received PY - 2014/12/10/entrez PY - 2014/12/10/pubmed PY - 2015/9/19/medline KW - Brønsted acids KW - asymmetric catalysis KW - domino reactions KW - organocatalysis KW - xanthenes SP - 2348 EP - 52 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 21 IS - 6 N2 - 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. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/25488376/Brønsted_acid_catalyzed_highly_enantioselective_addition_of_enamides_to_in_situ_generated_ortho_quinone_methides:_a_domino_approach_to_complex_acetamidotetrahydroxanthenes_ DB - PRIME DP - Unbound Medicine ER -