(4S)-p-hydroxybenzyl-1,3-oxazolidin-2-one as a solid-supported chiral auxiliary in asymmetric 1,3-dipolar cycloadditions

Tetrahedron Letters

Volumn 41, Issue 8, 2000, Pages 1265-1269

  Faita, Giuseppe ^a   Paio, Alfredo ^b   Quadrelli, Paolo ^a   Rancati, Fabio ^a   Seneci, Pierfausto ^b  

^a UNIVERSITY OF PAVIA   (Italy)

^b GSK   (Italy)

Author keywords

Asymmetric induction; Cycloadditions; Oxazolidinones; Solid phase synthesis

Indexed keywords

NITRILE; NITRONE; OXAZOLIDINONE DERIVATIVE; OXIDE; RESIN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; CONTROLLED STUDY; DIPOLE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034685257     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02265-0     Document Type: Article

References (15)

1. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
2. Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217.
3. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
4. Burgess, K.; Lim, D. Chem. Commun. 1997, 785.
5. Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777.
6. Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655.
7. Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935.
8. Lewis, N.; McKillop, A.; Taylor, R. J. K.; Watson, R. J. Synth. Commun. 1995, 25, 561.
9. 10 8.6 (c 0.5, ethanol)].
10. Bayston, D. J.; Frase, J.; Ashton, M. R.; Baxter, A. D.; Polywaka, M. E. C.; Moses, E. J. Org. Chem. 1998, 63, 3137.
11. 1H MAS NMR giving spectra in full accordance with the proposed structures.
12. Prashad, M.; Har, D.; Kim, H.-Y.; Repic, O. Tetrahedron Lett. 1998, 39, 7067.
13. Desimoni, G.; Faita, G.; Mella, M.; Righetti, P.; Zema, M. Tetrahedron 1999, 55, 8509.
14. 3 gave superimposable results with those obtained under uncatalysed condition.
15. Look, G. C.; Holmes, C. P.; Chinn, J. P.; Gallop, M. A. J. Org. Chem. 1994, 59, 7588.