Diastereoselectivity of the cyclization of hexos-5-uloses by Sm2-mediated pinacol coupling

Tetrahedron Letters

Volumn 39, Issue 14, 1998, Pages 2021-2024

  Adinolfi, Matteo ^a   Barone, Gaspare ^a   Iadonisi, Alfonso ^a   Mangoni, Lorenzo ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

MONOSACCHARIDE;

ARTICLE; COMPLEX FORMATION; CROSS LINKING; CYCLIZATION; MOLECULAR INTERACTION; STEREOCHEMISTRY;

EID: 0032473816     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00161-0     Document Type: Article

References (11)

1. 1. Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767-11780.
2. 2. Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Letters 1991, 32, 1125-1128.
3. 3. Perrin, E.; Mallet, J-M.; Sinaÿ, P. Carbohydr. Letters. 1996, 1, 215-216.
4. 4. Angyal, S. J. Adv. Carbohydr. Chem. Biochem. 1991, 42, 19-36.
5. 5. The Swern oxidation step was performed as in reference 1, but in THF as the solvent.
6. 6. Molander, G. A.; Kenny, C. J. Org. Chem. 1988, 53, 2132-2134.
7. 7. For sake of clarity, the carbon numbering of alditols 9-11 is retained for compounds 12a-14.
8. 8. Chiara, J. L.; Martinez, S.; Bernabé, M. J. Org. Chem. 1996, 61, 6848-6849.
9. 9. For other procedures to obtain hexos-5-uloses see Baxter, E. W., Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185; Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F. Tetrahedron 1997, 53, 8665-8674; and references cited therein.
10. 9. For other procedures to obtain hexos-5-uloses see Baxter, E. W., Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185; Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F. Tetrahedron 1997, 53, 8665-8674; and references cited therein.
11. 13C NMR, MS). The stereochemistry of the new centres was determined by NOE studies.