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The Ion Tag Strategy as a Route to Highly Efficient Organocatalysts for the Direct Asymmetric Aldol Reaction
Author(s) -
Lombardo Marco,
Easwar Srinivasan,
Pasi Filippo,
Trombini Claudio
Publication year - 2009
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.200800608
Subject(s) - aldol reaction , chemistry , catalysis , organocatalysis , proline , organic chemistry , combinatorial chemistry , enantioselective synthesis , amino acid , biochemistry
The installation of an imidazolium tag via acetate connection to the C‐4 of cis ‐4‐hydroxy‐ L ‐proline provides a highly efficient catalyst for the direct asymmetric aldol reaction, that works in a remarkably low catalyst loading (0.1 mol%) affording TONs up to 930 in the case of electron‐poor aromatic aldehydes with ee up to >99%.