Oxazoline N-oxide-mediated [2+3] cycloadditions: New access to quaternary asymmetric centres

European Journal of Organic Chemistry

Volumn , Issue 21, 2002, Pages 3566-3572

  Collon, Stéphane ^a   Kouklovsky, Cyrille ^a   Langlois, Yves ^a  

^a CNRS   (France)

Author keywords

Asymmetric synthesis; Cycloaddition; Oxazoline N oxide

Indexed keywords

OXAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036845357     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200211)2002:21<3566::AID-EJOC3566>3.0.CO;2-F     Document Type: Article

References (20)

1. For reviews on [2+3] cycloadditions, see: [1a]P. Deshong, S. W. Lander, Jr., J. M. Leginus, C. M. Dicken, in Advances in Cycloaddition (Ed.: D. P. Curran); JAI Press: Greenwich, 1988; vol. 1, pp. 87-128.
2. [1b] W. Carruthers, Clycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990.
3. [1c] R. D. Little, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming); Pergamon Press: Oxford, 1991; vol. 5, pp. 239-270.
4. [1d] A. Padwa, Intermolecular 1,3-dipolar cycloadditions. In Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press; Oxford, 1991; vol. 4, Chapter 9, pp. 1069-1109.
5. [1e] K. V. Gothelf, K. A. Jorensen, Chem. Rev. 1998, 98, 863-909.
6. O. Dirat, C. Kouklovsky, M. Mauduit, Y. Langlois, Pure Applied Chem. 2000, 72, 1721-1737.
7. C. Kouklovsky, O. Dirat, T. Berranger, Y. Langlois, M.-E. Tran Huu Dau, C. Riche, J. Org. Chem. 1998, 63, 5123-5128.
8. T. Berranger, Y. Langlois, J. Org. Chem. 1995, 60, 1720-1726.
9. S. W. Baldwin, R. B. McFayden, J. Aubé, J. D. Wilson, Tetrahedron Lett. 1991, 32, 4431-4433.
10. Esters 8a-8c were prepared by Steglich esterification of the corresponding acid, see Exp. Sect. Cyclobutenecarboxylic acid was obtained in two steps from commercially available cyclobutanecarboxylic acid, according to: W G. Dauben, J. R. Wiseman, J. Am. Chem. Soc. 1967, 89, 3545-3549.
11. Ester 5a was obtained by protection of the corresponding known alcohol: H.-S. Byun, K. C. Reddy, R. Bittman, Tetrahedron Letters 1994, 35, 1371-1374. Ester 5b was prepared by nucleophilic substitution of the known tert-butyl 2-(bromomethyl)acrylate with sodium benzyloxide: B. Giese, T. Linker, Synthesis 1992, 46-48.
12. Ester 5a was obtained by protection of the corresponding known alcohol: H.-S. Byun, K. C. Reddy, R. Bittman, Tetrahedron Letters 1994, 35, 1371-1374. Ester 5b was prepared by nucleophilic substitution of the known tert-butyl 2-(bromomethyl)acrylate with sodium benzyloxide: B. Giese, T. Linker, Synthesis 1992, 46-48.
13. [8a] K. Takeda, I. Imaoka, E. Yoshii, Tetrahedron 1994, 50, 10839-10848.
14. [8b] W. R. Roush, B. B. Brown, J. Org. Chem. 1992, 57, 3380-3387.
15. [8c] W. Adam, R. Albert, L. Hasemann, V. O. N. Salgado, B. Nestler, E.-M. Peters, F. Prechtl, H. G. von Schnering, J. Org. Chem. 1991, 56, 5782-5785.
16. [8d] F. Fotiadu, F. Michel, G. Buono, Tetrahedron Lett. 1990, 31, 4863-4867.
17. [8e] For a recent example in the α-methylene lactam series, see: J. Ishihara, M. Horie, Y. Shimada, S. Tojo, A. Murai, Synlett 2002, 403-406.
18. [9a] D. Alonso-Perarnau, P. de March, M. el Arrad, M. Figueredo, J. Font, T. Parella, Tetrahedron 1997, 53, 14763-14772.
19. [9b] P. Dalla Croce, R. Ferraccioli, C. La Rosa, Heterocycles 1995, 40, 349-355.
20. [9c] A. Sk, Ali, M. I. Wazeer, Tetrahedron Lett. 1992, 33, 3219-3222.