Tandem Michael addition and intramolecular aldol cyclization of 1,2-dideoxy-1-nitroheptitols derived from sugars

Tetrahedron Letters

Volumn 46, Issue 21, 2005, Pages 3673-3676

  Berrocal, M V ^a   Gil, M V ^a   Roman E ^a   Serrano, J A ^a   Hursthouse, M B ^b   Light, M E ^b  

^a UNIVERSITY OF EXTREMADURA   (Spain)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Aldol cyclization; Michael addition; Nitro compounds; Sugars

Indexed keywords

ACROLEIN DERIVATIVE; CYCLOHEXANOL DERIVATIVE; KETONE DERIVATIVE;

ALDOL REACTION; ARTICLE; CYCLIZATION; MICHAEL ADDITION; QUANTUM YIELD; STEREOCHEMISTRY;

EID: 17844374887     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.162     Document Type: Article

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12. 2O exchangeable, J = 2.5 Hz) at ca. 3.8 ppm suggests that the minor products could be another two stereoisomeric 2-acyl-1-methyl-4-glyco-4-nitrocyclohexanols
13. E.L. Eliel, and S.H. Wilen Stereochemistry of Organic Compounds 1994 Wiley-Interscience New York pp 696-697
14. 3-1)
15. int = 0.1293). The structure was solved by direct methods with SHELXS97 (Sheldrick, G. M. Acta Cryst. 1990, A 46, 467) and refined by full matrix least squares using SHELXL97 (Sheldrick, G. M. Program for Crystal Structure Refinement; University of Göttingen: Germany, 1997). X-ray crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (CCDC 166186), which are available free of charge from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK
16. int = 0.1293). The structure was solved by direct methods with SHELXS97 (Sheldrick, G. M. Acta Cryst. 1990, A 46, 467) and refined by full matrix least squares using SHELXL97 (Sheldrick, G. M. Program for Crystal Structure Refinement; University of Göttingen: Germany, 1997). X-ray crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (CCDC 166186), which are available free of charge from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK
17. 3CO-2)
18. 13: C, 52.17; H, 5.90; N, 2.64. Found: C, 52.45; H, 6.01; N, 2.57
19. We observed that when the pure crystalline nitroaldehyde 7c (or 8c) was treated for 30 min in acetonitrile, at room temperature, with 1 equiv of DBU, the resulting product consisted in a ca. 1:1 mixture of the starting material and aromatic 9c
20. +; 530.1880
21. +: 497.1670