Chiral N-phosphonyl imine chemistry: asymmetric additions of malonate-derived enolates to chiral N-phosphonyl imines for the synthesis of β-aminomalonates

Tetrahedron Letters

Volumn 50, Issue 9, 2009, Pages 1079-1081

  Chen, Zhong Xiu ^a   Ai, Teng ^a   Kaur, Parminder ^a   Li, Guigen ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

Aminomalonates; Dimethyl malonate; N Phosphonyl imines; Phosphoramide

Indexed keywords

IMINE; LITHIUM DERIVATIVE; MALONIC ACID DERIVATIVE; NAPHTHYL GROUP; PHOSPHONIUM DERIVATIVE; TRIFLUOROACETIC ACID;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; DIASTEREOISOMER; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 58149503411     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.12.093     Document Type: Article

References (28)

1. Lee M.-R., Raguse T.L., Schinerl M., Pomerantz W.C., Wang X., Wipf P., and Gellman S.H. Org. Lett. 9 (2007) 1801-1804
2. Liu M., and Sibi M.P. Tetrahedron 58 (2002) 7991-8035
3. Iijima K., Katada J., and Hayashi Y. Bioorg. Med. Chem. Lett. 9 (1999) 413-418
4. Bai R.L., Verdier-Pinard P., Gangwar S., Stessman C.C., McClure K.J., Sausville E.A., Pettit G.R., Bates R.B., and Hamel E. Mol. Pharmacol. 59 (2001) 462-469
5. Shapirot R. J. Org. Chem. 58 (1993) 5759-5764
6. Studer P., Larras V., and Riess G. Eur. Polym. J. 44 (2008) 1714-1721
7. Enders D., Moser M., Geibel G., and Laufer M.C. Synthesis (2004) 2040-2046 and references cited therein
8. Kochi T., Tang T.P., and Ellman J.A. J. Am. Chem. Soc. 125 (2003) 11276-11282
9. Córdova A. Acc. Chem. Res. 37 (2004) 102-112
10. Kobayashi S., and Ishitani H. Chem. Rev. 99 (1999) 1069-1094 and references cited therein
11. Kobayashi S., Ueno M., Saito S., Mizuki Y., Ishitani H., and Yamashita Y. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5476-5481
12. Akiyama T., Itoh J., Yokota K., and Fuchibe K. Angew. Chem., Int. Ed. 43 (2004) 1566-1568
13. Josephsohn N.S., Snapper M.L., and Hoveyda A.H. J. Am. Chem. Soc. 126 (2004) 3734-3735
14. Kobayashi S., Matsubara R., Nakamura Y., Kitagawa H., and Sugiura M. J. Am. Chem. Soc. 125 (2003) 2507-2515
15. Lou S., Taoka B.M., Ting A., and Schaus S.E. J. Am. Chem. Soc. 127 (2005) 11256-11257
16. Hamashima Y., Sasamoto N., Hotta D., Somei H., Umebayashi N., and Sodeoka M. Angew. Chem., Int. Ed. 44 (2005) 1525-1529
17. Uraguchi D., and Terada M. J. Am. Chem. Soc. 126 (2004) 5356-5357
18. Marigo M., Kjaersgaard A., Juhl K., Gathergood N., and Jorgensen K.A. Chem. Eur. J. 9 (2003) 2359-2367
19. Song J., Wang Y., and Deng L. J. Am. Chem. Soc. 128 (2006) 6048-6049
20. Kattuboina A., and Li G. Tetrahedron Lett. 49 (2008) 1573-1577
21. Kattuboina A., Kaur P., Ai T., and Li G. Chem. Biol. Drug Des. 71 (2008) 216-223
22. Han J.l., Ai T., and Li G. Synthesis 16 (2008) 2519-2526
23. Han J.L., Ai T., Nguyen T., and Li G. Chem. Biol. Drug Des. 72 (2008) 120-126
24. Lattanzi A. Tetrahedron: Asymmetry 17 (2006) 837-841
25. Ooi T., Ohara D., Fukumoto K., and Maruoka K. Org. Lett. 15 (2005) 3195-3197
26. Tillman A.L., and Ye J. Chem. Commun. (2006) 1191-1193
27. 3, 202 MHz): δ 26.27.
28. 3): δ 7.33-7.22 (m, 5H), 6.13 (s, br, 1H), 5.49 (s, br, 1H), 3.93 (d, J = 4.2 Hz, 1H), 3.75 (s, 3H), 3.64 (s, 3H), 1.42 (s, 9H).