On the mechanism of catalytic asymmetric dihydroxylation (AD) of alkenes

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 35, Issue 11, 1996, Pages 1119-1122

  Lohray, Braj B ^a   Bhushan, Vidya ^a   Nandanan, E ^a  

^a DR REDDY S RESEARCH FOUNDATION   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2842548197     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (38)

1. (a) Lohray B B, Tetrahedron Asymmetry, 3, 1992, 1317.
2. (b) Johnson R A & Sharpless K B, in: Catalytic asymmetric synthesis, edited by I Ojima (VCH, Weinheim) 1993, p.227-272.
3. (c) Kolb H C, VanNieuwennze M S & Sharpless K B, Chem Rev, 94, 1994, 2483.
4. (d) Jayamma Y, Nandanan E & Lohray B B, J Indian Inst Sci, 74, 1994, 309.
5. Corey E J & Lotto G I, Tetrahedron Lett, 31, 1990, 2665.
6. (a) Lohray B B & Bhushan V, Tetrahedron Lett, 33, 1992, 5113.
7. (b) Lohray B B & Bhushan V, Tetrahedron Lett, 34, 1993, 3911.
8. (a) Corey E J, Noe M C & Sarshar S, J Am Chem Soc, 115, 1993, 3828.
9. (b) Kolb H C, Andeersson P G, Bennani Y L, Crispino G A, Jeong K S, Wong H L & Sharpless K B, J Am Chem Soc, 115, 1993, 12226.
10. (a) Corey E J & Noe M C, J Am Chem Soc, 115, 1993, 12579.
11. (b) Kolb H C, Anderson P G & Sharpless K B, J Am Chem Soc, 116, 1994, 1278.
12. (a) Norrby P-O, Kolb H C & Sharpless K B, Organometallic, 13, 1994, 344.
13. (b) Norrby P-O, Kolb H C & Sharpless K B, J Am Chem Soc, 116, 1994, 8470.
14. (c) Becker H, Ho P T, Kolb H C, Loren S, Norrby P-O & Sharpless K B, Tetrahedron Lett, 35, 1994, 7315
15. (d) Pearlstein R M, Blackburn B K, Davies W M & Sharpless K B, Angew Chem Int Ed Engl, 29, 1990, 639.
16. (e) Göbel T & Sharpless K B, Angew Chem Int Ed Engl, 32, 1993, 1329.
17. (f) Andersson P G & Sharpless K B, J Am Chem Soc, 115, 1993, 7047.
18. (g) Becker H, King S B, Taniguchj M, Vanhessche K P M & Sharpless K B, J Org Chem, 60, 1995, 3940.
19. (h) Becker H, Soler M A & Sharpless K B, Tetrahedron, 51, 1995, 1345.
20. (i) Norrby P-O, Becker H & Sharpless K B, J Am Chem Soc, 118, 1996, 35.
21. (a) Corey E J, Noe M C & Sarshar S, Tetrahedron Lett, 35, 1994, 2861.
22. (b) Corey E J, Noe M C & Grogan M J, Tetrahedron Lett, 35, 1994, 6427.
23. (c) Corey E J, Guzman-Perez A & Noe M C, J Am Chem Soc, 116, 1994, 12109.
24. (d) Corey E J, Guzman-Perez A & Noe M C, J Am Chem Soc, 117, 1995, 10805.
25. (e) Corey E J, Noe M C & Guzman-Perez A, J Am Chem Soc, 117, 1995, 10817.
26. (f) Corey E J, Noe M C & Guzman-Perez A, Tetrahedron Lett, 36, 1995, 4171.
27. (g) Corey E J & Noe M C, J Am Chem Soc, 118, 1996, 319.
28. Deslongchamps P, Stereoelectrnnic effect in organic chemistry(Pergamon Press, Oxford)1983.
29. Khan S D & Hehre W J, J Am Chem Soc, 107, 1987, 666 and references cited therein.
30. Lohray B B, Bhushan V & Nandanan E, Tetrahedron Lett, 35, 1994, 4209.
31. (a) Burley S K & Petsko G A, Adv Protein Chem, 39, 1988, 125.
32. (b) Saenger W, Principles of nucleic acid structure (Springer Verlag, New York) 1984, p.132.
33. (c) For phenomenon of molecular recognition utilizing attractive interaction, see: Bioorganic chemistry frontiers, edited by H Dugas (Springer Verlag, Berlin)1991.
34. (d) For host-guest complexation through aromatic interaction, see: Frontiers in supramolecular organic chemistry and photochemistry, edited by H-J Scheider & H Dürr (VCH, Weinheim, Germany) 1991.
35. (e) In enantioselective Diels-Alder reaction, attractive interactions between Lewis acid and dienophiles are well known, for example, see: Evans D A, Chapman K T & Bisaha J J, J Am Chem Soc, 110, 1988, 1238; Corey E J & Loh T P, J Am Chem Soc, 113, 1991, 8966; Corey E J, Loh T P, Roper T D, Azimioara M D & Noe M C, J Am Chem Soc, 114, 1992, 8290.
36. (e) In enantioselective Diels-Alder reaction, attractive interactions between Lewis acid and dienophiles are well known, for example, see: Evans D A, Chapman K T & Bisaha J J, J Am Chem Soc, 110, 1988, 1238; Corey E J & Loh T P, J Am Chem Soc, 113, 1991, 8966; Corey E J, Loh T P, Roper T D, Azimioara M D & Noe M C, J Am Chem Soc, 114, 1992, 8290.
37. (e) In enantioselective Diels-Alder reaction, attractive interactions between Lewis acid and dienophiles are well known, for example, see: Evans D A, Chapman K T & Bisaha J J, J Am Chem Soc, 110, 1988, 1238; Corey E J & Loh T P, J Am Chem Soc, 113, 1991, 8966; Corey E J, Loh T P, Roper T D, Azimioara M D & Noe M C, J Am Chem Soc, 114, 1992, 8290.
38. 2-PHAL in which two DHQDs are closer by ca 2.5 Å.