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First anti ‐Selective Direct Michael Addition of α‐Alkoxy Ketones to Enones by Cooperative Catalysis of Samarium(III) Trifluoromethanesulfonate and Tributyltin Methoxide
Author(s) -
Esumi Naoto,
Nishimoto Yoshihiro,
Yasuda Makoto
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700501
Subject(s) - chemistry , michael reaction , alkoxy group , trifluoromethanesulfonate , aldol reaction , catalysis , methoxide , organic chemistry , lewis acids and bases , sodium methoxide , medicinal chemistry , alkyl
A new highly anti ‐diastereoselective Michael addition of α‐alkoxy ketones to α,β‐unsaturated ketones was achieved. This method features a dual‐catalyst protocol that combines samarium(III) trifluoromethanesulfonate and Bu 3 SnOMe. The combination of these two catalysts effectively allowed the generation of enolate species from α‐alkoxy ketones and produced Michael adducts in high yields with high anti diastereoselectivity. A variety of enones and α‐alkoxy ketones were applied to this system to give the anti products. One‐pot domino Michael/aldol reactions effectively afforded cyclic enones with a defined configuration.