A chiral phosphine–olefin ligand derived from l-hydroxyproline and its use in the rhodium-catalyzed asymmetric 1, 4-addition. Issue 12 (15th July 2015)

• Record Type: Journal Article
• Authors: Gandi, Vasudeva Rao; Lu, Yixin; Hayashi, Tamio
• Is Part Of: Tetrahedron, asymmetry. Volume 26:Issue 12/13(2015)
• Page Start: 679
• Page End: 682
• Publication Date: 2015-07-15
• Subjects: Asymmetry (Chemistry) -- Periodicals; 547.005
• DOI: 10.1016/j.tetasy.2015.05.004
• Languages: English
• ISSNs: 0957-4166

Abstract

Graphical abstract: Abstract: A new chiral phosphine–olefin ligand ( S )-1 has been designed and synthesized froml -hydroxyproline via a short reaction sequence. It was examined for its efficiency in the rhodium-catalyzed asymmetric addition of arylboronic acids and a phenylzinc reagent to cyclic α, β-unsaturated ketones, giving 1, 4-addition products with high enantioselectivities. Abstract : ( S )- tert -Butyl 2-((diphenylphosphino)methyl)-2, 5-dihydro-1 H -pyrrole-1-carboxylate: C12 H26 NO2 P [ α ]D 25 = −54 ( c 1.0, CHCl3 ) Source of chirality:l -Hydroxyproline Absolute configuration: ( S ) Abstract : ( S )- tert -Butyl 2-((tosyloxy)methyl)-2, 5-dihydro-1 H -pyrrole-1-carboxylate: C17 H23 NO5 S [α]D 25 = −117 ( c 1.10, CHCl3 ) Source of chirality:l -Hydroxyproline Absolute configuration: ( S )