Premium
Sequential Stereoselective Catalysis: Two Single‐Flask Reactions of a Substrate in the Presence of a Bifunctional Chiral Ligand and Different Transition Metals
Author(s) -
Annunziata Rita,
Benaglia Maurizio,
Cinquini Mauro,
Cozzi Franco,
Puglisi Alessandra
Publication year - 2003
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.200390201
Subject(s) - chemistry , stereoselectivity , stereocenter , bifunctional , cyclopropanation , dihydroxylation , ligand (biochemistry) , catalysis , stereochemistry , substrate (aquarium) , transition state , alkene , combinatorial chemistry , oxazoline , enantioselective synthesis , organic chemistry , biochemistry , oceanography , receptor , geology
A new bifunctional ligand capable of promoting different stereoselective catalytic transformations in combination with different transition metals has been prepared by connecting with a spacer a bis(oxazoline) to dihydroquinidine; this ligand was employed in a one‐flask procedure in which methyl ( E )‐3‐(4‐vinylphenyl)propenoate underwent first cyclopropanation at the electron‐rich double bond and then dihydroxylation at the electron‐poor alkene to afford a product containing four stereocenters with complete regiocontrol and high stereoselectivity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)