Remarkable effects of titanium tetrachloride in diastereoselective aza Diels-Alder cycloaddition: Synthesis of (S)-piperazic acid

Tetrahedron Letters

Volumn 46, Issue 4, 2005, Pages 555-558

  Makino, Kazuishi ^a   Henmi, Yoshiaki ^a   Terasawa, Makiko ^a   Hara, Osamu ^b   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

^b MEIJO UNIVERSITY   (Japan)

Author keywords

Aza Diels Alder cycloaddition; Chiral diene; Piperazic acid; Titanium chloride

Indexed keywords

ACID; ALKADIENE; PIPERAZIC ACID; TITANIUM TETRACHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLOADDITION; DIELS ALDER REACTION; STEREOCHEMISTRY; SYNTHESIS;

BETULACEAE;

EID: 11144348968     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.003     Document Type: Article

References (22)

1. D.L. Boger, and S.N. Weinreb Hetero Diels-Alder Methodology in Organic Synthesis 1987 Academic New York
2. K. Makino, Y. Henmi, and Y. Hamada Synlett 2002 613 615
3. K. Makino, T. Suzuki, S. Awane, O. Hara, and Y. Hamada Tetrahedron Lett. 43 2002 9391 9395
4. K. Makino, T. Suzuki, and Y. Hamada Bull. Chem. Soc. Jpn. 77 2004 1649 1653
5. K. Makino, T. Goto, Y. Hiroki, and Y. Hamada Angew. Chem., Int. Ed. 43 2004 882 884 and references cited therein
6. For a review on synthesis of piperazic acids, see: M.A. Ciufolini, and N. Xi Chem. Soc. Rev. 27 1998 437 445
7. K.J. Hale, J. Cai, V. Delisser, and S. Manariazar Tetrahedron Lett. 33 1992 7613 7616
8. Y. Aoyagi, Y. Saitoh, T. Ueno, M. Horiguchi, and K. Takeya J. Org. Chem. 68 2003 6899 6904
9. Y. Henmi, K. Makino, Y. Yoshitomi, O. Hara, and Y. Hamada Tetrahedron: Asymmetry 15 2004 3477 3481
10. K. Bevan, J.S. Davies, C.H. Hassall, R.B. Morton, and D.A.S. Philips J. Chem. Soc. (C) 1971 514 522
11. C.E. Adams, D. Aguilar, S. Hertel, W.H. Knight, and J. Paterson Synth. Commun. 18 1988 2225 2231
12. I.A. Aspinall, P.M. Cowley, G. Mitchell, and R.J. Stoodley J. Chem. Soc., Chem. Commun. 1993 1179 1180
13. M. Bols, R.G. Hazell, and I.B. Thomsen Chem. Eur. J. 3 1997 940 947
14. I.A. Aspinall, P.M. Cowley, G. Mitchell, C.M. Raynor, and R.J. Stoodley J. Chem. Soc., Perkin Trans. 1 1999 2591 2599
15. X. Liang, and M. Bols J. Org. Chem. 64 1999 8485 8488
16. H. Urabe, K. Kusaka, D. Suzuki, and F. Sato Tetrahedron Lett. 43 2002 285 289
17. A. Zhang, Y. Kan, and B. Jiang Tetrahedron 57 2001 2305 2309
18. t-BuOCl is completely consumed with quantitative production of PTAD (see Table 1, entry 5)
19. 4, the starting diene unexpectedly remained in the reaction, and therefore the yield was moderate
20. M.L. Zhao, E. Mano, Z. Song, D.M. Tschaen, E.J. Grabowski, and P.J. Reider J. Org. Chem. 64 1999 2564 2566
21. 4: C, 34.43; H, 4.54; N, 11.47. Found: C, 34.32; H, 4.46; N, 11.38
22. K.J. Hale, J. Cai, V. Delisser, S. Manariazar, S.A. Peak, G.S. Bhatia, T.C. Collins, and N. Jogiya Tetrahedron 52 1996 1047 1068