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Tetrahydroisoquinoline‐Based N ‐Oxides as Chiral Organocatalysts for the Asymmetric Allylation of Aldehydes
Author(s) -
Naicker Tricia,
Arvidsson Per I.,
Kruger Hendrik G.,
Maguire Glenn E. M.,
Govender Thavendran
Publication year - 2011
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.201100923
Subject(s) - chemistry , tetrahydroisoquinoline , enantioselective synthesis , yield (engineering) , organocatalysis , organic chemistry , aldehyde , catalysis , materials science , metallurgy
The short synthesis of a series of novel chiral N ‐oxideorganocatalysts and their evaluation in the asymmetric allylation reaction of aromatic and α‐β‐unsaturated aldehydes with allyltrichlorosilane is reported. These readily modifiable organocatalysts are the first of their kind based on the tetrahydroisoquinoline framework. The chiral homoallyl products were obtained with good chemical efficiency (up to 93 % yield) and high enantioselectivity (up to 91 % ee ) under mild reaction conditions (23 °C).