Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1995-12-14
1999-11-09
Burn, Brian M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
564488, C07C20944
Patent
active
059818026
ABSTRACT:
The subject invention provides a method of preparing an allylic amine having the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each independently hydrogen, halogen, cyano, nitro, linear or branched chain alkyl, aryl, etc.; wherein each alkyl or arylalkyl if present is independently unsubstituted or substituted by fluoro, cyano, nitro, linear or branched chain acyl, dialkylamino, etc.; wherein each aryl if present is independently unsubstituted or substituted by fluoro, cyano, nitro, linear or branched chain alkyl, arylmercapto, etc.; and wherein each of R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 optionally is covalently bonded linking pairwise a suitable atom from each to form from 0 to about 10 rings, wherein each ring contains between about four and about twelve atoms, using disubstituted sulfur diimides prepared in situ. Also provided are methods of preparing cyclic allylic amines in which allylic double bonds are endocyclic and exocyclic.
REFERENCES:
Brimble and Heathcock (1993) Allylic Amination by the Lewis-Acid-Mediated Ene Reaction of Diethyl Azodicarboxylate with Alkenes. J. Org. Chem. 58:5261-5263.
Bussas, R. and Kresze, G. (1982) Synthese von 2-Alkensulfinamiden-Struktur-Reactivitates-Beziehungen fur N-Sulfinylverbindungen als Enophile.
Deleris et al. (1988) Direct Regiospecific Allylic Aminaiton via Silicon Induced Pericyclic Reactions. A Novel Synthesis of Gamma Vinyl Gaba. Tetrahedron 44:4243-4258.
Garigipati et al. (1984) Diastereoselective systhesis of Unsaturated Vicinal Amino Alcohols via Diels-Alder Reactions of N-Sulfinyl Dienophiles. J. Am. Chem. Soc. 106:7861-7867.
Hancock, John and Markert, A.R. (1966) Azo and Hydrazo Compounds. III.sup.1,2 Bis(Ethoxycarbonyl) Sulfurdiimine and Ethyl N-Sulfinyl Carbamate.
Hanson, P. and Stockburn, W.A. (1985) 1,2-Thiazines and Related Heterocycles. J. Chem. Soc., Perkin Trans. II pp. 589-595.
Hori, T. et al, (1978) Allylic Deuteration and Tritiation of Olefins With N-Sulfinylsulfonamides. J. Org. Chem. 43:1456-1459.
Johannsen, M and Jorgensen, K.A. (1994) Iron-Catalyzed Allylic Amination. J. Org. Chem. 59:214-216.
Katz, Thomas J. and Shi, Shuhao (1994) A Simple Allylic Amination Procedure and the Metathesis of N-Sulfinylcarbamates J. Org. Chem. 59:8297-8298.
Keck, Gary E. et al. (1981) A Versatile Method for Carbon-Nitrogen Bond Formation Via Ene Reactions of Acylnitrogen Compounds. Tetrahedron (23):4007-4016.
Kresze, G. and Munsterer, H., (1983) Bis(methoxycarbony)sulfur Diimide, a Convient Reagent for the Allylic Amination of Alkenes J. Org. Chem. 48:3561-3564.
Kresze, G. and Wucherpfennig, W. (1967) Organic Syntheses with Imides of Sulfur Dioxide. Angew. Chem. Int. Ed. Engl. 6(2):149-167.
Kresze, G. et al. (1993) Organic Synthesis Collect. vol. 8, pp. 427-430.
Levchenko, E.S. and Dorokhova, E.M. (1972) Derivatives of Thionyl Imide and Diiminosulfur. J. Org. Chem. USSR (Engl. Transl.) 8:2573-2577.
Levchencko, E.S., et al. (1967) Bisalkoxycarbonylsulfur Diimides. J. Org. Chem. USSR (Engl. Transl.) 3:2014-2019.
Minami, T. et al. (1968) The Chemistry of Cumulated Double Bond Compounds IV the Reaction of Sulfurdiimides With Triethylphosphite. Tetrahedron Letters 26:3049-3051.
Sharpless, K.B. and Hori, Tetsuo (1976) Allylic Amination of Olefins and Acetylenes by Imido Sulfur Compounds. J. Org. Chem. 41:176-177.
Singer, Stephen P. and Sharpless, K. Barry (1978) Synthesis of dl-Gabaculine Utilizing Direct Allylic Amination as the Key Step. J. Org. Chem. 43:1448-1455.
Whitesell, James K. and Yaser, H. Kenan (1991) Asymmetric Induction in Allylic Amination. J. Am. Chem. Soc. 113:3526-3529.
Burn Brian M.
The Trustees of Columbia University in the City of New York
White John P.
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