Computer assisted, mechanism directed design of a new ligand for the highly enantioselective catalytic addition of diethylzinc to aldehydes

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8773-8776

  Vidal Ferran, Anton ^a   Moyano, Albert ^a   Pericàs, Miquel A ^a   Riera, Antoni ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; LIGAND; PIPERIDINE DERIVATIVE;

ARTICLE; COMPUTER SIMULATION; DRUG DESIGN; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR MODEL;

EID: 0030783295     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10348-3     Document Type: Article

References (12)

1. Vidal-Ferran, A.; Moyano, A.; Pericàs, M.A.; Riera, J. Org. Chem. 1997, 62, 4970-4982.
2. Gao, Y.; Hanson, R.M.; Klunder, J.M.; Ko, S.Y.; Masamune, H.; Sharpless, K.B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
3. (a) Asymmetric Catalysis in Organic Synthesis; Noyori, R.; John Wiley & Sons, Inc.: New York, 1994, ch. 5, p. 255-297.
4. (b) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69.
5. (c) Soai, K. Chem. Rev. 1992, 92, 833-856.
6. Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327-6335.
7. These terms refer to the anti-or syn-relationship between the two terminal rings in the tricyclic system.
8. Dewar, M.J.S.; Zoebish, E.G.; Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
9. Dewar, M.J.S.; Merz, K.M., Jr. Organometallics 1988, 7, 522-524.
10. The calculations were performed with the Restricted-Hartree-Fock (RHF) version of AMI as implemented in the MOPAC module in the CERIUS2 package of programs (BIOSYM/Molecular Simulations, San Diego, California).
11. The N-Zn distance was kept constant at the value optimized for R=H.
12. 4) and concentrated in vacuo, and the residue was purified by bulb-to-bulb distillation to give 2.58 g of (S)-1-phenylpropanol (95% yield): e.e. 97%, selectivity 99%. The chiral ligand was recovered (99 %) by chromatography of the distillation residue.