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A New Robust and Efficient Ion‐Tagged Proline Catalyst Carrying an Amide Spacer for the Asymmetric Aldol Reaction
Author(s) -
Montroni Elisa,
Sanap Shrihari P.,
Lombardo Marco,
Quintavalla Arianna,
Trombini Claudio,
Dhavale Dilip D.
Publication year - 2011
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.201100595
Subject(s) - chemistry , aldol reaction , catalysis , proline , amide , aldol condensation , combinatorial chemistry , enantioselective synthesis , organocatalysis , organic chemistry , amino acid , biochemistry
The synthesis of a new, highly efficient cis ‐ion‐tagged catalyst ( 8a ), possessing an amide linkage between the imidazolium tag and the proline ring, is described. This new bench‐stable catalyst has been tested in the classic asymmetric aldol condensation between ketones and aldehydes “in the presence” of water, and is proposed as a valuable alternative to the analogous but more sensitive ester cis‐ 2d . Catalyst 8a displayed an excellent efficiency in terms of catalyst loading and stereochemical control.