1,3-Dipolar cycloadditions to unsaturated organoboranes. III - Regio- and stereocontrolled access to boronic ester substituted isoxazolidines.

Tetrahedron Letters

Volumn 38, Issue 38, 1997, Pages 6665-6668

  Carboni, Bertrand ^a   Ollivault, Morgane ^a   Bouguenec, Frédéric Le ^a   Carrié, Robert ^a   Jazouli, Mohamed ^b  

^a UNIVERSITÉ DE RENNES 1   (France)

^b FACULTÉ DES SCIENCES   (Morocco)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOBORON DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; DIASTEREOISOMER; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030775574     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01560-8     Document Type: Article

References (25)

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2. Tuffariello, J.J. in "1,3-Dipolar Cycloaddition Chemistry", A. Padwa Ed., Wiley, New York, 1984, p 83-168. Torsell, K.B.G. in "Nitrile oxides, Nitrones and Nitronates in Organic synthesis", VCH, New York, 1988. Confalone, P.N.; Huie, E.M. Org. React., 1988, 36, 1-173. Pawda, A. in "Comprehensive Organic Synthesis", Trost, B.M.; Fleming I. Eds, Pergamon Press, Oxford, 1991, Vol 4, p 1069-1109. Wade, P.A. in "Comprehensive Organic Synthesis", Trost, B.M.; Fleming I., Pergamon Press, Oxford, 1991, Vol 4, p 1111-1168. Frederickson, M. Tetrahedron 1997, 53, 403-425.
3. Tuffariello, J.J. in "1,3-Dipolar Cycloaddition Chemistry", A. Padwa Ed., Wiley, New York, 1984, p 83-168. Torsell, K.B.G. in "Nitrile oxides, Nitrones and Nitronates in Organic synthesis", VCH, New York, 1988. Confalone, P.N.; Huie, E.M. Org. React., 1988, 36, 1-173. Pawda, A. in "Comprehensive Organic Synthesis", Trost, B.M.; Fleming I. Eds, Pergamon Press, Oxford, 1991, Vol 4, p 1069-1109. Wade, P.A. in "Comprehensive Organic Synthesis", Trost, B.M.; Fleming I., Pergamon Press, Oxford, 1991, Vol 4, p 1111-1168. Frederickson, M. Tetrahedron 1997, 53, 403-425.
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5. Tuffariello, J.J. in "1,3-Dipolar Cycloaddition Chemistry", A. Padwa Ed., Wiley, New York, 1984, p 83-168. Torsell, K.B.G. in "Nitrile oxides, Nitrones and Nitronates in Organic synthesis", VCH, New York, 1988. Confalone, P.N.; Huie, E.M. Org. React., 1988, 36, 1-173. Pawda, A. in "Comprehensive Organic Synthesis", Trost, B.M.; Fleming I. Eds, Pergamon Press, Oxford, 1991, Vol 4, p 1069-1109. Wade, P.A. in "Comprehensive Organic Synthesis", Trost, B.M.; Fleming I., Pergamon Press, Oxford, 1991, Vol 4, p 1111-1168. Frederickson, M. Tetrahedron 1997, 53, 403-425.
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16. Huisgen H., Hauck H., Seidl H., Burger M. Chem. Ber. 102:1969;1117-1128.
17. 4 (435.4) : C, 71.73 ; H, 7.87 ; N, 3.22. Found : C, 71.7 ; H, 7.9 ; N, 2.9.
18. It is interesting to compare the regiochemical course of the cycloaddition of 3i with the tendency of crotonates to afford the corresponding isoxazolidines bearing the carboxyl group at the 4-position .
19. -3, μ(MoKα)= 0.83 Å, T=294K, F(000);= 928, R = 0.059 for 2342 reflections. X-ray crystallographic data have been deposited at the Cambridge Crystallographic Data Centre.
20. 2) ; 74.0 (CH) ; 79.0 (Cα to B) ; 84.9 (C) ; 115.8 (CH) ; 122.2 (CH) ; 128.9 (CH) ; 129.0 (CH) ; 129.3 (CH) ; 129.5 (CH) ; 130.2 (CH) ; 130.3 (CH) ; 133.5 (CH) ; 137.5 (C) ; 143.3 (C) ; 152.0 (C) ; 198.1 (CO).
21. 2) ; 54.4 (CH) ; 114.0 (CH) ; 118.8 (CH) ; 128.3 (CH) ; 128.7 (CH) ; 128.8 (CH) ; 129.5 (CH) ; 133.5 (CH) ;133.6 (CH) ; 135.1 (C) ;136.6 (C) ; 146.3 (C) ; 197.9 (CO) ; 199.1 (CO).
22. Inouye Y., Watanabe Y., Takahashi S., Kakisawa H. Bull. Chem. Soc. Jap. 52:1979;3763-3764.
23. Krol W.J., Mao S., Steel D.L., Townsend C.A. J. Org. Chem. 56:1991;728-731.
24. Brady, O.L.; Dunn, F.P.; Goldstein, R.F. J. Chem. Soc. 1926, 2386-2403.
25. 2) ; 78.9 (CH) ; 83.5 (CH) ; 84.9 (CH) ; 114.1 (CH) ; 121.9 (CH) ; 128.7 (CH) ; 129.2 (CH) ; 129.4 (CH) ; 133.6 (CH) ; 135.0 (C) ; 150.7 (C) ; 196.7 (CO).