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A Highly Enantio‐ and Diastereoselective Synthesis of Spirocyclic Dihydroquinolones via Domino Michael Addition‐Lactamization of ortho ‐Quinone Methide Imines
Author(s) -
Hodík Tomáš,
Schneider Christoph
Publication year - 2018
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.201803886
Subject(s) - quinone methide , chemistry , domino , cascade reaction , michael reaction , combinatorial chemistry , enantioselective synthesis , phosphoric acid , reactive intermediate , catalysis , organic chemistry , stereochemistry , quinone
Abstract Spirocyclic dihydroquinolones have been obtained with good yields and excellent diastereoselectivity (>20:1 d.r.), and enantioselectivity (up to 99:1 e.r.) from in situ generated ortho ‐quinone methide imines and cyclic β‐oxo esters. This one‐step domino Michael addition–lactamization process features mild reaction conditions, easily accessible starting materials, and products with two adjacent chiral centers one of which is quaternary. Mechanistic studies revealed the in situ generated chiral magnesium phosphate salt rather than the free phosphoric acid to be the more reactive catalyst for this reaction.