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Direct Asymmetric α‐Amination of Cyclic Ketones Catalyzed by Siloxyproline
Author(s) -
Hayashi Yujiro,
Aratake Seiji,
Imai Yoshinaga,
Hibino Kazuhiro,
Chen QiYin,
Yamaguchi Junichiro,
Uchimaru Tadafumi
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200700307
Subject(s) - amination , catalysis , chemistry , proline , yield (engineering) , organic chemistry , amino acid , combinatorial chemistry , materials science , biochemistry , metallurgy
trans ‐ tert ‐Butyldimethylsiloxy‐ L ‐proline displays greater catalytic activity and affords higher enantioselectivity than the parent proline in the α‐amination reaction of carbonyl compounds with azodicarboxylate. A quantum mechanical calculation reveals the structure of the transition state. In the presence of a catalytic amount of siloxyproline and water (3–9 equiv), α‐amino carbonyl derivatives, which are important synthetic intermediates, are obtained in good yield and with excellent enantioselectivity.