Regio- and diastereoselective boron-mediated aldol reactions of chiral α,β,γ,δ-unsaturated N-acyloxazolidinones

Tetrahedron Asymmetry

Volumn 9, Issue 24, 1998, Pages 4313-4324

  Takacs, James M ^a   Jaber, Mohamad R ^a   Swanson, Benjamin J ^a   Mehrman, Steven J ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORON; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CHIRALITY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032564663     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00459-5     Document Type: Article

References (18)

1. Takacs, J. M.; Boito, S. C.; Myoung, Y.-C. Current Org. Chem. 1998, 2, 233-254.
2. Mehta, G.; Rao, H. S. P. In The Chemistry of Functional Groups: The Chemistry of Polyenes and Dienes; Rappoport, Z. Ed.; Wiley: New York, 1997; Vol. 1, pp. 359-480.
3. Takacs, J. M.; Weidner, J. J. J. Org. Chem. 1994, 59, 6480-6483.
4. Takacs, J. M.; Jaber, M. R.; Clement, F.; Walters, C. J. Org. Chem. 1998, 63, 6757-6760.
5. Evans, D. A.; Sjogren, E. B.; Bartroli, J.; Dow, R. L. Tetrahedron Lett. 1986, 27, 4957-4960.
6. Mead, K. T.; Park, M. Tetrahedron Lett. 1995, 36, 1205-1208.
7. Chattopadhyay, S. K.; Pattenden, G. Tetrahedron Lett. 1995, 36, 5271-5274.
8. We found that freshly prepared dibutylboron triflate often gave much more satisfactory results than the commercial samples we used. For the preparation of dibutylboron triflate, see: Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099-3111.
9. Roush, W. R. Adv. Cycloaddit. 1990, 2, 91-146.
10. Schneider, C.; Rehfeuter, M. Tetrahedron 1997, 53, 133-144.
11. Abarbi, M.; Parrin, J.-L.; Cintrat, J.-C.; Duchene, A. Synthesis 1996, 82-86.
12. Dreiding, A. S.; Pratt, R. J. J. Am. Chem. Soc. 1953, 75, 3717.
13. Concepcion, A. B.; Maruoka, K.; Yamamoto, H. Tetrahedron 1995, 51, 4011-4020.
14. Piers, E.; Jung, G. L.; Ruediger, E. H. Can. J. Chem. 1987, 65, 670-682.
15. Bellasoued, M.; Salemkour, M. Tetrahedron 1996, 52, 4607-4624.
16. For other applications of the LiOH-promoted Horner-Wadsworth-Emmons reaction of phosphonocrotonates, see reference 4 and: Bonadies, F.; Cardilli, A.; Lattanzi, A.; Orelli, L. R.; Scettri, A. Tetrahedron Lett. 1994, 35, 3383-3386.
17. Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron: Asymmetry 1994, 5, 961-974.
18. Lee, E.; Hur, C. U.; Park, J. H. Tetrahedron Lett. 1989, 30, 7219-7220.