New isoxazolidine-based chiral auxiliaries for asymmetric syntheses

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3261-3264

  Abiko, Atsushi ^b   Liu, Ji Feng ^a   Wang, Guo Qiang ^a   Masamune, Satoru ^b  

^a KAO CORPORATION   (Japan)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ISOXAZOLIDINE DERIVATIVE;

ALKYLATION; ARTICLE; DRUG PURIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030893752     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00580-7     Document Type: Article

References (19)

1. (a) Abiko, A.; Moriya, O.; Filla, S. A.; Masamune, S. Angew. Chem. Int. Ed. Engl. 1995, 34, 759.
2. (b) Abiko, A.; Davis, W. M.; Masamune, S. Tetrahedron: Asymmetry 1995, 6, 1295.
3. (c) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077.
4. (d) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1081.
5. Abiko, A.; Masamune, S. Tetrahedron Lett. 1992, 33, 5517.
6. Hassner, A.; Maurya, R.; Mesko, E. Tetrahedron Lett. 1988, 29, 5313.
7. 2SnO catalyzed nitrone formation with 5-hydroxypentanal oxime afforded the unexpected ene-products. Abiko, A. Chemistry Letters, 1995, 357.
8. For preparative purpose, the oxime was used as a mixture of isomers. The major isomer of the oxime cyclized with high selectivity (-20:1), but the minor isomer less selectively (-5:1). The selectivities for the cyclization to 2b and 2d were exo:endo=10:1.
9. 3).
10. (a) Hassner, A.; Maurya, R.; Friedman, O.; Gottlieb, H. E.; Padwa, A.; Austin, D. J. Org. Chem. 1993, 58, 4539.
11. (b) Aurich, H. G.; Frenzen, G.; Gentes, C. Chem. Ber. 1993, 126, 787.
12. ref la, Id. See also, (a) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L.J. Am. Chem. Soc. 1994, 116, 9361.
13. (b) Deccico, C. P.; Grover, P. J. Org. Chem. 1996, 61, 3534.
14. 3).
15. Abiko, A.; Liu, J.-F.; Masamune, S. J. Org. Chem. 1996, 61, 2590.
16. Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. in press.
17. The corresponding tertiary amines were formed <5%.
18. For the aldol products (10-12), β-hydroxy group was protected as methoxymethyl ether before reaction.
19. As preliminary experiments Horner-Emmons reaction with 4-tert-butylcyclohexanone (see ref le) and Lewis acid mediated Diels-Alder reaction of the acrylate derivative with cyclopentadiene were found to proceed with high selectivities.