Enantioselective synthesis of (S)-α-arylpropionic acids via Pd-catalyzed kinetic resolution of benzylic alcohols

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 44, Issue 3, 2005, Pages 557-562

  Thakur, Vinay V ^a   Sudalai, A ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ALCOHOL; IBUPROFEN; NAPROXEN; PALLADIUM; PHENYLPROPIONIC ACID DERIVATIVE; PROPIONIC ACID DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; KINETICS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 17444371251     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (38)

1. (a) Sonawane H R, Bellur N S, Ahuja J R & Kulkarni D G, Tetrahedron Asymmetry, 3, 1992, 163.
2. (b) Rieu J-P, Boucherie A, Cousse H & Mouzin G, Tetrahedron, 42, 1986, 4095.
3. (a) Shen T Y, Angew Chem Int. Ed Engl, 6, 1972, 460.
4. (b) Harrison I T, Lewis B, Nelson P, Rooks W, Roszkowski A, Tomolonis A & Fried J H, J Med Chem 13, 1970, 203.
5. Dentsch D, Chemtech 1991, 157.
6. (a) Garcia M, del Campo C, Llama E F, Sanchez-Montero J M & Sinisterra V, Tetrahedron, 49, 1993, 8433.
7. (b) Camps P & Gimenez S, Tetrahedron Asymmetry, 6, 1995, 991.
8. Bando T, Namba Y & Shishido K, Tetrahedron Asymmetry 8, 1997, 2159.
9. Cleij M, Archelas A & Furstoss R, J Org Chem, 64, 1999, 5029.
10. (e) Bhattacharya G, Mandal S & Nag S, Tetrahedron Asymmetry, 11, 2000, 2403.
11. (a) Hiyama T & Wasaka N, Tetrahedron Lett, 26, 1985, 3259.
12. (b) Noyori R, Nagai K & Kitamura M, J Org Chem, 52, 1987, 3174.
13. Piccolo O, Spreafico F, Vesentin G & Valoti E, J Org Chem, 52, 1987, 10.
14. Stille J K & Parrinetto G, J Am Chem Soc, 109, 1987, 7122
15. (e) Fuji K, Node M, Tanaka F & Hosoi S, Tetrahedron Lett, 30, 1989, 2825.
16. (f) Giordano C, Castaldi G, Cavicchioli S & Villa M, Tetrahedron, 45, 1989, 4243.
17. (g) Takono S, Yanase M & Ogasawara K, Heterocycles, 29, 1989, 1349.
18. (h) Coghlan D R, Hamon P G, Massy W R A & Slobedman D, Tetrahedron Asymmetry, 1, 1990, 295.
19. Alper H & Nathalie H, J Am Chem Soc, 112, 1990, 2803.
20. (j) Piccolo O, Spereafico T & Visenten G, J Org Chem, 56, 1991, 183.
21. (k) Kumar A, Salunkhe R V, Rane R A & Dike S Y, J Chem Soc Chem Commun, 1991, 485.
22. Hamon D P G, Massy-Westropp R A & Newton J L, Tetrahedron Asymmetry, 4, 1993, 1435.
23. Sonawane H R, Bellur N S, Kulkarni D G & Ayyangar N R, Tetrahedron, 50, 1994, 1243.
24. (n) Griesbach R C, Hamon D P G & Kennedy R J, Tetrahedron Asymmetry, 8, 1997, 507.
25. (o) Jung M E & Anderson K L, Tetrahedron Lett, 38, 1997, 2605.
26. (p) Nandanan E, Jayachandran B, Phukan P, Pais G C G & Sudalai A, Indian J Chem, 37B, 1998, 1221.
27. (q) Ishibashi H, Maeki M, Yagi J, Ohba M & Kanai T, Tetrahedron, 55, 1999, 6075.
28. (r) Hodous B L, Ruble J C & Fu G C, J Am Chem Soc, 121, 1999, 2637.
29. (s) Chen A, Ren L, & Crudden C M, J Org Chem, 64, 1999, 9704.
30. (t) Carde L, Davies D H & Roberts S M, J Chem Soc Perkin Trans, 1, 2000, 2455.
31. (a) Collet A, Enantiomer, 4, 1999, 157.
32. (b) Wistuba D & Schurig V, J Chromatogr, A, 875, 2000, 255.
33. Keith J M, Larrow J F & Jacobsen E N, Adv Synth Catal, 343, 2001, 5.
34. (a) Jensen D R, Pugsley J S & Sigman M S, J Am Chem Soc, 123, 2001, 7475.
35. (b) Ferreira E M & Stoltz B M, J Am Chem Soc, 123, 2001, 7725.
36. Barton D H R, Martell A E & Sawyer D T, The Activation of Dioxygen and Homogenous Catalytic Oxidation; (Plenum Press, New York), 1993.
37. McNamara J M & Gleason W B, J Org Chem, 41, 1976, 10711.
38. Casalnuovo A L, Rajan Babu T V, Ayers T A & Warren T H, J Am Chem Soc, 116, 1994, 9869.