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Enantioselective addition of diethylzinc to N-diphenylphosphinoylimines employing N,N-dialkyl-1,2-diphenyl-2-aminoethanols as chiral ligands

โœ Scribed by Xiaomei Zhang; Liuzhu Gong; Aiqiao Mi; Xin Cui; Yaozhong Jiang; Michael C. K. Choi; Albert S. C. Chan

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
80 KB
Volume
42
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

By fine-tuning the substituents on the nitrogen of (1S,2R) and (1R,2S)-1,2-diphenyl-2-aminoethanols, a chiral ligand 2b was obtained, which showed excellent enantioselectivity, with up to 94% e.e, for the asymmetric addition of diethylzinc to N-diphenylphosphinoylimines 1. In one example, the optically active amide 3c was converted into a new amine 5 with 98% e.e. by a reaction sequence involving Suzuki coupling and hydrolysis without racemization.

๐Ÿ“œ SIMILAR VOLUMES

Enantioselective addition of diethylzinc
Enantioselective addition of diethylzinc to a N-diphenylphosphinoylimine employing cinchona alkaloids as chiral ligands
โœ Kenneth J.M. Beresford ๐Ÿ“‚ Article ๐Ÿ“… 2002 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 91 KB

The use of cinchona alkaloids to promote the addition of diethylzinc to P,P-diphenyl-N-(phenylmethylene)phosphinic amide has been examined. Using cinchonine and cinchonidine as ligands, the S and R enantiomers of N-(1-phenylpropyl)-P,Pdiphenylphosphinic amide were prepared in good yield with up to 9