Stereoselective synthesis of protected ketohexoses via aldol reaction of chiral dioxanone enolate

Synlett

Volumn , Issue 9, 1999, Pages 1447-1449

  Majewski, Marek ^a   Nowak, Pawel ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Chiral lithium amides; Dioxanone; Enantioselective deprotonation

Indexed keywords

AMIDE; BORON; KETOSE; LITHIUM;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032873166     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2862     Document Type: Article

References (13)

1. (a) Majewski, M.; Gleave, D. M.; Nowak, P. Can. J. Chem. 1995, 73, 1616.
2. (b) Majewski, M.; Lazny, R.; Nowak, P. Tetrahedron Lett. 1995, 36, 5465.
3. (a) Jurczak, J. and Zamojski, A. in Preparative Carbohydrate Chemistry, Hanessian, S., Ed.; Marcel Dekker, New York, 1997; p. 593.
4. (b) Collins, P.; Ferrier, R. Monosaccharides: Their Chemistry and Their Roles in Natural Products, Wiley, New York 1995; p. 53.
5. Majewski, M.; Gleave, D. M. Tetrahedron Lett. 1989, 30, 5681.
6. Moon Kim, B.; Williams, S. F.; Masamune, S. in Comprehensive Organic Synthesis, vol. 2, Heathcock, C. H., Ed.; Pergamon, Oxford, 1991; p. 239.
7. Review: O'Brien, P. J. J. Chem. Soc., Perkin Trans. 1, 1998, 1439.
8. Chiral lithium amides having a fluoroalkyl substituent were developed by Koga: Aoki, K.; Koga, K. Tetrahedron Lett. 1997, 38, 2505 and references therein.
9. Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem. Int. Ed. Engl. 1985, 24, 1; see also ref. 4, p. 181.
10. (a) Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron, 1986, 42, 447.
11. (b) Roush, W.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 294.
12. These studies will be described in the full paper
13. The differences in ee reported in Table 2, entries 9-11 are small but statistically significant. Each experiment was repeated 3-5 times and with careful control of experimental conditions reproducibility within 2% was obtained.