Catalytic enantioselective cyclopropanation with bis(halomethyl) zinc reagents. II. The effect of promoter structure on selectivity
The catalytic, enantioselective cyclopropanation of cinnamyl alcohol has been accomplished with bis (iodomethyl)zinc in the presence of chiral bis(sulfonamides) derived from cyclohexanediamine. An extensive survey of diamine and sulfonamide structure has revealed a marked sensitivity to the spatial relationship of the amine groups, but only a modest dependence on the sulfonamide residue.
Denmark, Scott E.,Christenson, Beritte L.,O'Connor, Stephen P.
p. 2219 - 2222
(2007/10/02)
Catalytic Asymmetric Addition of Polyfunctional Dialkylzincs to β-Stannylated and β-Silylated Unsaturated Aldehydes
The addition of functionalized dialkylzincs to readily available β-stannylated or β-silylated unsaturated aldehydes in the presence of a catalytic amount of (1R,2R)-1,2-bis(trifluorosulfonamido)cyclohexane (8 mol percent) provides chiral allylic alcohols
Ostwald, Roswitha,Chavant, Pierre-Yves,Stadtmueller, Heinz,Knochel, Paul
p. 4143 - 4153
(2007/10/02)
A Catalytic Enantioselective Reaction Using a C2-Symmetric Disulfonamide as a Chiral Ligand: Alkylation of Aldehydes Catalyzed by Disulfonamide-Ti(O-i-Pr)4-Dialkyl Zinc System
Excellent enantioselective alkylation of aldehydes with dialkylzinc has been developed.This methodology is based on the concept of modifying the Lewis acid with a C2-symmetric, electron-withdrawing disulfonamide.The chiral Lewis acid catalysts used in the present study are the titanium complexes, prepared in-situ from disulfonamide and Ti(O-i-Pr)4.Key Words: Chiral disulfonamide; chiral titanium complex; enantioselective alkylation; dialkyl zinc; catalytic reaction