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Functionalized Chiral Ionic Liquid Catalyzed Asymmetric S N 1 α‐Alkylation of Ketones and Aldehydes
Author(s) -
Zhang Long,
Cui Lingyun,
Li Xin,
Li Jiuyuan,
Luo Sanzhong,
Cheng JinPei
Publication year - 2010
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.201000609
Subject(s) - chemistry , desymmetrization , kinetic resolution , pyrrolidine , ionic liquid , catalysis , alkylation , enantioselective synthesis , enamine , yield (engineering) , organocatalysis , organic chemistry , aldol reaction , ionic bonding , medicinal chemistry , ion , materials science , metallurgy
Pyrrolidine‐derived functionalized chiral ionic liquids (FCILs) have been found to catalyze asymmetric S N 1 α‐alkylations of ketones and aldehydes with up to 99 % yield, >99:1 dr and 87 % ee . The FCIL catalysts enable S N 1 α‐alkylations of cyclic ketones, particularly of 3‐ and 4‐substituted cyclohexanones with excellent diastereoselectivity and good enantioselectivity, featuring unprecedented desymmetrization and kinetic resolution processes for these types of asymmetric reaction. Full details of this study as well as the proposed enamine transition‐state are presented.