A study of transesterification of chiral (-)-pinanediol methylboronic ester with various structurally modified diols

Monatshefte fur Chemie

Volumn 138, Issue 8, 2007, Pages 747-753

  Roy, Chandra D ^a,b   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

^b EMD Biosciences Inc   (United States)

Author keywords

Boronic ester; Diol; Pinanediol; Transesterification

Indexed keywords

EID: 34547497641     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-007-0681-7     Document Type: Article

References (41)

1. PJ Duggan EM Tyndall 2002 J Chem Soc Perkin Trans 1 1325
2. DG Hall 2005 Boronic Acids: Preparations and Applications in Organic Synthesis and Medicine Wiley-VCH Weinheim
3. DS Matteson 1995 K Hafner CW Rees BM Trost JM Lehn PVR Schleyer Stereodirected Synthesis with Organoboranes Springer-Verlag Heidelberg
4. W Yang X Gao B Wang 2003 Medicinal Research Reviews 23 346
5. a) Brown HC, Zweifel G (1961) J Am Chem Soc 83: 486;
6. b) Brown HC, Ramachandran PV (1995) J Organomet Chem 500: 1
7. a) Matteson DS (1989) Tetrahedron 45: 1859;
8. b) Matteson DS (1991) Pure Appl Chem 63: 339;
9. c) Matteson DS, Man HW (1996) J Org Chem 61: 6047;
10. d) Matteson DS (1999) Chemtech 29: 6;
11. e) Matteson DS (1999) J Organomet Chem 581: 51;
12. f) Kotha S, Lahiri K, Kashinath D (2002) Tetrahedron 58: 9633
13. a) Brown HC, Rangaishenvi MV (1988) J Organomet Chem 358: 15;
14. b) Matteson DS, Ray R, Rocks RR, Tsai DJS (1983) Organometallics 2: 1536;
15. c) Matteson DS, Ray R (1980) J Am Chem Soc 102: 7590;
16. d) Rangaishenvi MV, Singaram B, Brown HC (1991) J Org Chem 56: 3286;
17. e) Brown HC, Bakshi RK, Singaram B (1988) J Am Chem Soc 110: 1529;
18. f) Brown HC, Singaram B, Cole TE (1985) J Am Chem Soc 107: 460;
19. g) Brown HC, Cole TE, Bakshi RK, Srebnik M, Singaram B (1986) Organometallics 5: 2303;
20. h) Matteson DS, Michnick TJ, Willett RD, Patterson CD (1989) Organometallics 8: 726;
21. i) Matteson DS, Sadhu KM, Lienhard GE (1981) J Am Chem Soc 103: 5241
22. SJ Coutts J Adams D Krolikowski RJ Snow 1994 Tetrahedron Lett 35 5109
23. a) Roy CD, Brown HC (2007) J Organomet Chem 692: 784;
24. b) Roy CD, Brown HC (2007) Tetrahedron Lett 48: 1959;
25. c) Roy CD, Brown HC (2007) Tetrahedron Submitted
26. R Ray DS Matteson 1980 Tetrahedron Lett 21 449
27. a) Coxon JM, Garland RP, Hartshorn MP (1970) Aust J Chem 23: 1069;
28. b) Hughes CR, MacSweeney DF, Ramage R (1971) Tetrahedron 27: 2247
29. MM Midland A Kazubski 1992 J Org Chem 57 2953
30. a) Brown HC, Bhat NG, Somayaji V (1983) Organometallics 2: 1311;
31. b) Brown HC, Cole TE (1983) Organometallics 2: 1316;
32. c) Brown HC, Singh SM (1986) Organometallics 5: 998
33. HC Brown GW Kramer AB Levy MM Midland 1975 Organic Syntheses via Borane John Wiley & Sons New York
34. E Wistuba C Ruchardt 1981 Tetrahedron Lett 22 4069
35. G Petris P Giacomello T Picotti A Pizzabiocca G Renzi M Speranza 1986 J Am Chem Soc 108 7491
36. SM Grayson BK Long S Kusomoto BP Osborn RP Callahan CR Chambers CG Willson 2006 J Org Chem 71 341
37. HS Kim K Begum N Ogura Y Wataya Y Nonami T Ito A Masuyama M Nojima KJ [tmp] McCullough 2003 J Med Chem 46 1957
38. E Kleinpeter H Kuhn M Muhlstadt 1976 Org Magn Reson 8 279
39. a) Partanem T, Maikonen PJ, Vainiotalo P, Vepsalainen J (1990) J Chem Soc Perkin Trans 2: 772;
40. b) Angyal SJ, Young RJ (1959) J Am Chem Soc 81: 5467
41. R Kraus G Spiteller 1991 Phytochemistry 30 1203