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Asymmetric Aldol Synthesis: Choice of Organocatalyst and Conditions
Author(s) -
Nakashima Erika,
Yamamoto Hisashi
Publication year - 2017
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.201601525
Subject(s) - aldol reaction , yield (engineering) , acetone , chemistry , proline , tetrazole , enantioselective synthesis , aldol condensation , organocatalysis , catalysis , organic chemistry , biochemistry , amino acid , materials science , metallurgy
This is the first report of a successful asymmetric aldol reaction of acetone and 4‐nitrobenzaldehyde catalyzed by only 0.01 mol % of proline tetrazole (5‐pyrrolidin‐2‐yltetrazole). Amazingly, 3 mol % of water as an additive has significantly improved the efficiency of the aldol reaction in terms of yield and enantioselectivity, up to a 0.1‐mol‐scale production (up to 99 % isolated yield, 84 % ee ).