Asymmetric synthesis of both enantiomers of α-methyl-α-methoxyphenylacetic acid from l-(+)-tartaric acid: formal enantioselective synthesis of insect pheromone (-)-frontalin

Tetrahedron Asymmetry

Volumn 17, Issue 13, 2006, Pages 1979-1984

  Prasad, Kavirayani R ^a   Chandrakumar, Appayee ^a   Anbarasan, Pazhamalai ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIKETONE; ALPHA METHYL ALPHA METHOXYPHENYLACETIC ACID; FRONTALIN; PHENYLACETIC ACID DERIVATIVE; PHEROMONE; REAGENT; TARTARIC ACID; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; GRIGNARD REACTION; PRECURSOR; PRIORITY JOURNAL;

EID: 33746986502     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.07.007     Document Type: Article

References (20)

1. Reviews:. Corey E.J., and Guzman-Perez A. Angew. Chem., Int. Ed. 37 (1998) 388
2. Fuji K. Chem. Rev. 93 (1993) 2037
3. Christoffers J., and Mann A. Angew. Chem., Int. Ed. 40 (2001) 4591
4. Prasad K.R., and Anbarasan P. Tetrahedron: Asymmetry 17 (2006) 1146
5. Prasad K.R., and Anbarasan P. Tetrahedron: Asymmetry 17 (2006) 850
6. Prasad K.R., and Anbarasan P. Tetrahedron Lett. 47 (2006) 1433
7. Prasad K.R., and Gholap S.L. Synlett (2005) 2260
8. Prasad K.R., and Gholap S.L. J. Org. Chem. 71 (2006) 3643
9. Prasad K.R., and Chandrakumar A. Tetrahedron: Asymmetry 16 (2005) 1897
10. Nugiel D.A., Jakobs K., Worley T., Patel M., Kaltenbach III R.F., Meyer D.T., Jadhav P.K., De Lucca G.V., Smyser T.E., Klabe R.M., Bacheler L.T., Rayner M.M., and Seitz S.P. J. Med. Chem. 39 (1996) 2156-2169
11. McNulty J., Grunner V., and Mao J. Tetrahedron Lett. 42 (2001) 5609
12. Prasad K.R., and Chandrakumar A. Synthesis (2006) 2159
13. Sen S.E., Roach S.L., Boggs J.K., Ewing G.J., and Magrath J. J. Org. Chem. 62 (1997) 6684
14. Angiolini L., Bazzarri P.C., and Tramontini M. Tetrahedron 25 (1969) 4211
15. Eliel E.L., and Frazee W.J. J. Org. Chem. 44 (1979) 3598
16. Use of both antipodes of acids 11a in the enantiomeric excess determination of secondary alcohols and amines was reported while the manuscript was under preparation. Kowalczyk R., and Skarżewski J. Tetrahedron: Asymmetry 17 (2006) 1370
17. N1 process involving a carbocation. Further investigations concerning the anomaly of the reactivity of the diastereomers are underway.
18. Kinzer G.W., Fentiman Jr. A.F., Page Jr. T.F., Foltz R.L., Vite J.P., and Pitman G.B. Nature 221 (1969) 447
19. Utility of diketone 12 in the synthesis unsaturated α-benzyloxy aldehydes and in the synthesis of insect pheromone exo-brevicomin was reported by us. Prasad K.R., and Anbarasan P. Tetrahedron: Asymmetry 15 (2005) 3951
20. Kang S.-K., Rho S.-H., and Namkoong E.-Y. Bull. Korean Chem. Soc. 16 (1995) 191