Lewis acid mediated asymmetric [2,3]-sigmatropic rearrangement of allylic amines. Scope and mechanistic investigation
摘要：
The first asymmetric [2,3]-sigmatropic rearrangement of achiral allylic amines has been realized by quaternization of the amines with an enantiomerically pure diazaborolidine and subsequent treatment with Et3N. The resultant homoallylic amines were obtained in good yields and excellent ee's. The observed diastereo- and enantioselectivities were rationalized by invoking a kinetically controlled process, and support for this model was obtained from an NMR spectroscopic investigation of the chiral Lewis acid-substrate complex. The structure of the Lewis acid-product complex was established by X-ray crystallographic analysis and supported the proposed mechanism.
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关键词：
3 sigmatropic rearrangement generated metal carbenoids ammonium ylides 3>-sigmatropic rearrangement diazo-compounds intramolecular reaction catalytic methods oxonium ylides
DOI：
10.1021/jo062178v
被引量：
年份：
2007
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