B,B-dihaloterpenylboranes as reagents for the diastereo- and enantioselective synthesis of syn-aldols

Tetrahedron Asymmetry

Volumn 8, Issue 9, 1997, Pages 1379-1382

  Ramachandran, P Veeraraghavan ^a   Xu, Wei Chu ^a   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETONE;

CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; SHORT SURVEY; STEREOCHEMISTRY;

EID: 0001296936     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00138-9     Document Type: Article

References (29)

1. For reviews on the aldol reactions, see: (a) Mukaiyama, T. Org. React. 1982, 28, 203.
2. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R.; Top. Stereochem. 1982, 13, 1.
3. (c) Heathcock, C. H. in Asymmetric Synthesis, Morrison, J. D. Ed., Academic Press, Orlando, FL, 1983, Vol.3, Chapter 2.
4. (d) Heathcock, C. H. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991, Vol. 2.
5. For reactions of achiral boron enolates, see: (e) Fenzl, W.; Koster, R. Liebigs Ann. Chem. 1975, 1322.
6. (f) Masamune, S.; Mori, S.; Van Horn, D.; Brooks, D. W. Tetrahedron Lett. 1989, 1665.
7. (g) Brown, H. C.; Dhar, R. K.; Bakshi, R. K.; Pandiarajan, P. K.; Singaram, B. J. Am. Chem. Soc. 1989, 111, 3441.
8. (h) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1992, 57, 3767.
9. (i) idem., ibid. 1993, 58, 147.
10. (j) Ganesan, K.; Brown, H. C. J. Org. Chem. 1993, 58, 7162.
11. (a) Hamana, H.; Sasakura, K.; Sugasawa, T. Chem. Lett. 1984, 1729.
12. (b) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871.
13. (c) Luke, G. P.; Morris, J. J. Org. Chem. 1995, 60, 3013.
14. Ramachandran, P. V.; Xu, W. C.; Brown, H. C. Tetrahedron Lett. 1997, 38, 769.
15. (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. in Topics in Stereochemistry; Wiley-Interscience, New York, 1982. Vol. 13, p.1.
16. (b) Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asym. 1995, 6, 2613.
17. Meyers, A. I.; Yamamoto, Y. J. Am. Chem. Soc. 1981, 103, 4278.
18. (b) Paterson, I.; Goodman, J. M.; Lister, M. A.; Schumann, R. C.; McLure, C. K.; Norcross, R. D. Tetrahedron 1990, 46, 4663.
19. Fringuelli, F.; Piermatti, O.; Pizzo, F. J. Org. Chem. 1995, 60, 7006.
20. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173.
21. 2 reagents, see: Brown, H. C.; Ramachandran, P. V.; Chandrasekharan, J. Heteroatom Chem. 1995, 7, 117.
22. 2 reagents, see: Brown, H. C.; Ramachandran, P. V.; Chandrasekharan, J. Heteroatom Chem. 1995, 7, 117.
23. 2 reagents, see: Brown, H. C.; Ramachandran, P. V.; Chandrasekharan, J. Heteroatom Chem. 1995, 7, 117.
24. Brown, H. C.; Ramachandran, P. V. In Advances in Asymmetric Synthesis Vol, 1., Hassner, A. Ed. JAI Press: Geenwich, CT, 1995, pp 147-210.
25. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
26. Brown, H. C.; Ramachandran, P. V.; Teodorovic', A. V.; Swaminathan, S. Tetrahedron Lett. 1991, 32, 6691.
27. Brown, H. C.; Randad, R. S.; Bhat, K. S.; Zaidlewicz, M.; Racherla, U. S. J. Am. Chem. Soc. 1990, 772, 2389.
28. 19F NMR spectrum of the MTPA ester.
29. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Syntheses via Boranes Wiley-Interscience: New York, 1975; Chapter 9.