A uniquely accessible route to the diastereoselective synthesis of azetine derivatives

Heterocycles

Volumn 62, Issue , 2004, Pages 217-222

  Ambhaikar, Narendra B ^a   Herold, Marike ^a   Liotta, Dennis C ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM; AZETIDINE DERIVATIVE; BORON; CHLOROTITANIUM; DIHYDROPYRIMIDINONE DERIVATIVE; IMINE; N METALLOALDIMINE DERIVATIVE; N PROPIONYLTHIAZOLIDINE 2 THIONE; NAPHTHYL GROUP; NITRILE; PHENYL GROUP; PYRIMIDINONE DERIVATIVE; THIAZOLIDINE 2 THIONEAZETINE DERIVATIVE; THIAZOLIDINE DERIVATIVE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG; ZIRCONIUM;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; OLIGOMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0346459983     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-s(p)56     Document Type: Article

References (15)

1. N. B. Ambhaikar, J. P. Snyder, and D. C. Liotta, J. Am. Chem. Soc., 2003, 125, 3690.
2. a) G. Cardillo and C. Tomasini, Chem. Soc. Rev., 1996, 117.
3. b) D. C. Cole, Tetrahedron, 1994, 50, 9517.
4. c) E. Juaristi, D. Quintana, and J. Escalante, Aldrichimica Acta, 1994, 27, 3.
5. (a) Y. Nagao, Y. Hagiwara, T. Kumagai, M. Ochiai, T. Inoue, K. Hashimoto, and E. Fujita, J. Org. Chem., 1986, 51, 2391.
6. (b) I. Ojima, I. Habus, M. Zhao, M. Zucco, Y. H. Park, C. M. Sun, and T. Brigaud, Tetrahedron, 1992, 48, 6985.
7. 2OS: C, 66. 63; H, 6.99; N, 9.71; O, 5.55; S, 11.12. Found: C, 67.37; H, 7.16; N, 9.19; O, 5.43; S, 10.77.
8. R. Bloch, Chem. Rev., 1998, 98, 1407.
9. (a) G. Cainelli, M. Panunzio, D. Giacomini, G. Martelli, and G. Spunta, J. Am. Chem. Soc., 1988, 110, 6879.
10. (b) G. Cainelli, M. Panunzio, C. Michele, D. Giacomini, E. Mezzina, and D. Giovagnoli, Tetrahedron, 1993, 49, 3809.
11. (c) G. Cainelli, M. Panunzio, P. Andreoli, G. Martelli, G. Spunta, D. Giacomini, and E. Bandini, Pure. & Appl. Chem., 1990, 62, 605.
12. M. Panunzio and P. Zarantonello, Org. Proc. Res. Dev., 1998, 2, 49.
13. P. Andreoli, L. Billi, G. Cainelli, M. Panunzio, G. Martelli, and G. Spunta, J. Org. Chem., 1990, 55, 4199.
14. 2ZrHCl) or 4 h (for DIBAL) at room temperature. Titanium tetrachloride (3.45 mmol) was added and the reaction mixture stirred for 1 h at room temperature. During this time, titanium enolate of compound (2) was generated by dissolving 2 in dry dichloromethane (5 mL) at 0 °C under argon, then dropwise addition of titanium tetrachloride (1.15 mmol), stirring for 5 min and the addition of (-)-sparteine (2.87 mmol). The brown solution was stirred for 40 min at 0 °C and then added to the first reaction mixture via a cannula. The reaction was stirred for 18 h at room temperature. The work up was the same as for the oxime ethers.
15. In a 25 mL ovendried flask under argon, nitrile (1.72 mmol) and (9-BBN)2 (1.72 mmol) were dissolved in dry toluene (3 mL) and refluxed for 4 h. The toluene was removed under vacuum and replaced with dry dichloromethane (2 mL). During this time, titanium enolate of compound (2) was generated by dissolving 2 in dry dichloromethane (5 mL) at 0 °C under argon, then dropwise addition of titanium tetrachloride (1.15 mmol), stirring for 5 min and the addition of (-)-sparteine (2.87 mmol). The brown solution was stirred for 40 min at 0 °C and to it was added the boronaldimine solution via a cannula. The reaction was stirred for 12 h at room temperature. The work up was the same as for the oxime ethers.