- A NOVEL SYNTHESIS OF 3,3-(SPIRO)SUBSTITUTED AZETIDINES
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A smooth and efficient new synthesis for 3,3-disubstituted azetidines, starting from readily available nitriles, was estabilished: α-hydroxymethylation of the starting materials, followed by O-tosylation and LiAlH4-reduction of the key intermediates thus obtained, led - via spontaneous cyclization of the intermediate amino derivatives - to 3,3-disubstituted azetidines.Scope and limitations of this new method were studied with respect to generalized applicability: the target compounds were accessible in good yields for a variety of starting materials (cyclic and acyclic di(hetero)aryl, (hetero)arylalkyl, dialkyl, as well as basic moieties).The products thus obtained may be of interest for ensuing conversions due to their unblocked nitrogen.
- Froehlich, Johannes,Sauter, Fritz,Blasl, Karin
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p. 1879 - 1892
(2007/10/02)
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