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Enantioselective Allylation of Aldehydes Catalyzed by Diastereoisomeric Bis(tetrahydroisoquinoline) N , N ′‐Dioxides
Author(s) -
Vlašaná Klára,
Hrdina Radim,
Valterová Irena,
Kotora Martin
Publication year - 2010
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.201001219
Subject(s) - chemistry , enantioselective synthesis , aldehyde , catalysis , isoquinoline , dichloromethane , tetrahydrofuran , tetrahydroisoquinoline , medicinal chemistry , solvent , asymmetric induction , organic chemistry , stereochemistry
Enantioselective allylation of aromatic and α,β‐unsaturated aldehydes with allyltrichlorosilane catalyzed by two diastereoisomeric ( R , R ax , R )‐ and ( R , S ax , R )‐bis‐1,1′‐[5,6,7,8‐tetrahydro‐3‐(tetrahydrofuran‐2‐yl)isoquinoline] N , N′ ‐dioxideswas studied. The course of the reaction was profoundly influenced by the chosen solvent. The ( R , S ax , R ) catalyst efficiently promoted the reaction in THF with enantioselectivity up to 96 %. On the other hand, the allylation of aromatic aldehydes in the presence of the ( R , R ax , R ) catalyst proceeded only in MeCN (up to 67 % ee ), and the level of asymmetric induction was strongly influenced by the presence of electron‐donating and ‐accepting groups in the aldehyde. The allylation of α,β‐unsaturated aldehydes proceeded only in dichloromethane (enantioselectivity up to 68 %).