Tetrahedron p. 7543 - 7556 (1994)
Update date:2022-08-04
Topics:
Bach, Karen K.
El-Seedi, Hesham R.
Jensen, Henrik M.
Nielsen, Helene B.
Thomsen, Ib
Torssell, B. G.
The principles of 1,2-cyano-hydroxylation of olefins were applied to the preparation of 1,2-cyano-amines.The dipole component of this cycloaddition was nitrile imines, which formed pyrazolines with olefins.Ring cleavage was accomplished by thermolysis of 3-carboxypyrazolines, which gave 1,2-cyano-amines and subsequent hydrolysis gave β-amino acids.The synthesis of the title reagents were described.Ethyl 2-chloro-2-ethoxy-acetate gave selectively oximes, hydrazones, nitrones, and phosphonium salts with hydroxylamine, hydrazines, N-substituted hydroxylamines and triphenylphosphine respectively.The phosphonium salt was used in a Wittig reaction with aldehydes to give α-ketoesters.Treatment of the acid chloride with allyl alcohols and subsequently with a monosubstituted hydroxylamine gave the allylic ester nitrone, which underwent intramolecular cyclization.Similarly, intramolecular cyclization were carried out with the allylic ester - nitrile oxime and allylic ester - nitrile imine systems.
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Doi:10.1016/j.saa.2013.12.016
(2014)Doi:10.1039/d0cc01815e
(2020)Doi:10.1002/anie.201308071
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(1994)