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Copper‐Catalyzed Asymmetric Alkylation of β‐Keto Esters with Xanthydrols
Author(s) -
Trillo Paz,
Baeza Alejandro,
Nájera Carmen
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300627
Subject(s) - chemistry , stereocenter , alkylation , trifluoromethanesulfonate , catalysis , copper , organic chemistry , enantioselective synthesis , kinetic resolution , combinatorial chemistry , medicinal chemistry
The copper(II) triflate‐ tert ‐butyl‐bisoxazoline [Cu(OTf) 2 ‐ t‐ Bu‐BOX]‐catalyzed asymmetric alkylation of β‐keto esters using free benzylic alcohols such as xanthydrols, as alkylating agents, is herein described for the first time. This green protocol renders in general the corresponding products with good results in terms of both yields and enantioselectivities using different keto esters, even when quaternary stereocenters were created. The scope, limitations and mechanistic aspects of the process are also discussed.