Highly enantioselective Michael reactions catalyzed by a chiral quaternary ammonium salt. Illustration by asymmetric syntheses of (S)-ornithine and chiral 2-cyclohexenones

Organic Letters

Volumn 2, Issue 8, 2000, Pages 1097-1100

  Zhang, Fu Yao ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; 2-CYCLOHEXEN-1-ONE; CYCLOHEXANONE DERIVATIVE; INORGANIC SALT; ORNITHINE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLOHEXANONES; MOLECULAR STRUCTURE; ORNITHINE; QUATERNARY AMMONIUM COMPOUNDS; SALTS; SPECTRUM ANALYSIS; STEREOISOMERISM;

EID: 0034689884     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0056527     Document Type: Article

References (14)

1. Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414.
2. Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000.
3. Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347.
4. Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
5. Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. Engl. 1999, 38, 1931.
6. Corey, E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287.
7. For earlier work on the enantioselective alkylation of the benzophenone Schiff base of tert-butyl elycinate see: (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353.
8. (b) O'Donnell, M. J.; Wu, S.; Huffman, J. C. Tetrahedron 1994, 50, 4507.
9. (c) Lipkowitz, K. B.; Cavanaugh, M. W.; Baker, B.; O'Donnell, M. J. J. Org. Chem. 1991, 56, 5181.
10. Heinzman, S. W.; Ganem, B. J. Am. Chem. Soc. 1982, 104, 6801.
11. + 348.1838, found 348.1827. The ee value was determined by HPLC analysis with a Regis Whelk-01 column, 20% isopropyl alcohol in hexane, 1.0 mL/min, l = 254 nm, retention times: minor, 9.3 min; major, 11.0 min.
12. (S)-3,5-Diphenyl-5-oxopentanoic acid (10) has previously been synthesized from a chiral starting material; see: Diaz-Ortiz, A.; Diez-Barra, E.; de la Hoz, A.; Prieto, P.; Moreno, A. J. Chem. Soc., Perkin Trans. 1 1996, 259.
13. + 359.1647, found 359.1631. The ee value was determined by HPLC analysis with a Chiralcel OD column, 10% isopropyl alcohol in hexane, 1.0 mL/min, λ = 254 nm, retention times: minor, 36.2 min; major, 54.0 min.
14. The only other catalytic route for the asymmetric synthesis of ornithine reported utilized Knowles-Monsanto-type reduction of an α-N-benzoylaminoacrylic acid derivative with a chiral Rh(I) catalyst; see: Baldwin, J. E.; Merritt, K. D.; Schofield, C. J. Tetrahedron Lett. 1993, 34, 3919.