Enantioselective addition of diethylzinc to a N-diphenylphosphinoylimine employing cinchona alkaloids as chiral ligands

Tetrahedron Letters

Volumn 43, Issue 40, 2002, Pages 7175-7177

  Beresford, Kenneth J M ^a  

^a DE MONTFORT UNIVERSITY   (United Kingdom)

Author keywords

Cinchona alkaloids; Diethylzinc; Enantioselective addition; N diphenylphospinoylimine

Indexed keywords

ALKALOID DERIVATIVE; AMIDE; DIETHYLZINC; DIPHENYLPHOSPHINOYLIMINE; IMINE; LIGAND; N (1 PHENYLPROPYL) P,P DIPHENYLPHOSPHINIC AMIDE; P,P DIPHENYL N (PHENYLMETHYLENE)PHOSPHINIC AMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CINCHONA; CYCLOADDITION; ENANTIOMER; ENANTIOSELECTIVITY;

CINCHONA;

EID: 0037201122     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01669-6     Document Type: Article

References (13)

1. Jacques J.K., Collet A., Wilen S.H. Enantiomers, Racemates and Resolution. 1981;John Wiley and Sons, New York.
2. Whitesell J.K. Chem. Rev. 89:1989;1581-1590.
3. Moser H., Rihs G., Sauter H. Z. Naturforsch. 37:1982;451-462.
4. For examples, see: Kobayashi S., Ishitani H. Chem. Rev. 99:1999;1069-1094. and references cited therein.
5. Jimeno C., Vidal-Ferran A., Moyano A., Pericás M.A., Riera A. Tetrahedron Lett. 40:1999;777-780.
6. Pinto P., Anderson P.G. Tetrahedron. 57:2001;1615-1618.
7. Sato I., Kodaka R., Soai K. J. Chem. Soc., Perkin Trans. 1. 2001;2912-2914.
8. Zhang X., Cong L., Mi A., Cui X., Jiang Y., Choi M.C.K., Chan A.S.C. Tetrahedron Lett. 42:2001;6369-6372.
9. Smaardijk A.A., Wynberg H. J. Am. Chem. Soc. 52:1987;135-137.
10. . For HPLC conditions and retention times, see: Anderson P.G., Guijarro D., Tanner D. J. Org. Chem. 62:1997;7364-7375.
11. . For preparation of 1, see: Jennings W.B., Lovely C.J. Tetrahedron. 47:1991;5561-5568.
12. . The free amine can be obtained from 1 by acidic hydrolysis, see: Ramage R., Hopton D., Parrot M.J., Kenner G.W., More G.A. J. Chem. Soc., Perkin Trans. 1. 1984;1357.
13. 4) and the solvent removed in vacuo. Flash chromatography on silica gel eluting with acetone: hexane (3:7 then 1:1) gave 2 as a white solid. Analytical data were in accordance with literature.