Novel chiral 1-phosphono-1,3-butadiene for asymmetric hetero Diels-Alder cycloadditions with nitroso and azodicarboxylate dienophiles

Tetrahedron Letters

Volumn 51, Issue 7, 2010, Pages 1052-1055

  Monbaliu, Jean Christophe ^a   Tinant, Bernard ^a   Peeters, Daniel ^a   Marchand Brynaert, Jacqueline ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Azodicarboxylate dienophiles; Chiral phosphonodienes; DFT calculation; Hetero Diels Alder reaction; Nitroso dienophiles

Indexed keywords

1,3 BUTADIENE DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; NITROSO DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; DRUG SYNTHESIS; STEREOCHEMISTRY; STEREOSPECIFICITY;

ALNUS;

EID: 73649131593     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.12.063     Document Type: Article

References (17)

1. Kukhar V., and Hudson H. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity (2000), John Wiley & Sons, Ltd
2. Monbaliu J.-C., Robiette R., Peeters D., and Marchand-Brynaert J. Tetrahedron Lett. 50 (2009) 1314-1317 and references cited therein
3. Monbaliu J.-C., and Marchand-Brynaert J. Synthesis 11 (2009) 1876-1880
4. Monbaliu J.-C., and Marchand-Brynaert J. Tetrahedron Lett. 49 (2008) 1839-1842
5. Fringuelli F., and Taticchi A. The Diels-Alder Reaction (2002), John Wiley & Sons, Ltd
6. Yamamoto H., and Kawasaki M. Bull. Chem. Soc. Jpn. 80 (2007) 595-607
7. Wyatt P.B., Villalonga-Barber C., and Motevalli M. Tetrahedron Lett. 40 (1999) 149-152
8. Cheng E.W.C., Mandalia R.T., Motevalli M., Mothia B., Patanwadia Y., and Wyatt P.B. Tetrahedron 62 (2006) 12398-12407
9. Katagiri N., Yamamoto M., Iwaoka T., and Kaneko C. J. Chem. Soc. Commun. (1991) 1429-1430
10. Ware R.W., and King S.B. J. Org. Chem. 65 (2000) 8725-8729
11. Maffei M., and Buono G. Tetrahedron 59 (2003) 8821-8825
12. Bennani Y., and Hanessian S. Tetrahedron 52 (1996) 13837-13866
13. Frisch M.J., et al. Gas phase calculations were done using the gaussian 98 suite of programs. Revision A.11 (1998), Gaussian, Pittsburgh, PA The single point PCM SCRF method is used to evaluate solvent effects
14. Domingo L.R., and Sàez J.A. Org. Biomol. Chem. 7 (2009) 3576-3583
15. Domingo L.R., Picher M.T., and Arroyo P. Eur. J. Org. Chem. (2006) 2570-2680 and references cited therein
16. For the cycloaddition 1c+2c, a strong hydrogen bond-like interaction appeared between the N-H moiety of the chiral auxiliary and the C{double bond, long}O bond of the dienophile.
17. Domingo L.R., Saéz J.A., Zaragozà R.J., and Arnò M. J. Org. Chem. 73 (2008) 8791-8799