Palladium catalyzed addition of amines to 3,4-epoxy-1-butene

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

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564 1, 564399, 564443, 564445, 564462, 564503, C07C21300

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active

052889106

ABSTRACT:
4-amino-2-buten-1-ol is formed by the regioselective addition of primary amines or ammonia to 3,4-epoxy-1-butene. A quantity of a the primary amine or ammonia is reacted with 3,4-epoxy-1-butene in a reaction medium in the presence of a catalyst. The reaction medium is a liquid which has an E.sub.T (30) no less than about 32. The catalyst is a complex of palladium and phosphine ligands.

REFERENCES:
patent: 4670557 (1987-06-01), Su
B. M. Trost et al., "A Synthesis of Substituted Pyrrolidines via a Palladium(2+)-Catalyzed Cyclization. An Unusual Approach to a Carbapenem," 108 J. Amer. Chem. Soc 6053-4 (1986).
B. M. Trost et al., "Steric Steering with Supported Palladium Catalysts," 100 J. Amer. Chem. Soc. 7779-7781 (1978).
J. Tsuji et al., "Regioselective 1,4-Addition of Nucleophiles to 1,3-Diene Monoepoxides Catalyzed by Palladium Complex," 22 Tetrahedron Letters 2575-8 (1981).
B. M. Trost et al., "Regiochemical Directing Efforts in Palladium Catalyzed Alkylations with Polyene Electrophilic Partners," 27 Tetrahedron Letters 4949-52 (1986).
J. Tsuji et al., "Palladium-Catalyzed Regioselective Reactions of Silyl-Substituted Allylic Carbonates and Vinyl Epoxide," 29 Tetrahedron Letters 343-6 (1988).
J. Tsuji, "New Synthetic reactions Catalyzed By Palladium Complexes," 58 Pure & Applied Chem. 869-78 (1986).
T. Tsuda, "Palladium-Catalyzed Reaction of 1,3-diene Monoepoxides with .beta.-keto Acids. Allylic Alkylation and Isomerization of 1,3-Diene Monoepoxides," 51 J. Org. Chem. 5216-21 (1986).
Trost et al., J. Am. Chem. Soc., vol. 103, pp. 5969-5972 (1981).
Tenaglia et al., Tetrahedron Letters, vol. 29, No. 38, pp. 4851-4854 (1988).

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