Sequential Stereoselective Catalysis: Two Single‐Flask Reactions of a Substrate in the Presence of a Bifunctional Chiral Ligand and Different Transition Metals | Zendy

Annunziata Rita | Zendy; Benaglia Maurizio | Zendy; Cinquini Mauro | Zendy; Cozzi Franco | Zendy; Puglisi Alessandra | Zendy

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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)

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