A new method for stereoselective homoallylic amine synthesis
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 13,p. 1433-1447
- https://doi.org/10.1039/p19930001433
Abstract
Nitrile oxide cycloadditions to readily available allylic diphenylphosphine oxides 2 proceeded regioselectively and stereoselectively to give 5-(1′-diphenylphosphinoylalkyl)isoxazolines 4 and 5. These heterocycles were reduced to δ-amino-β-hydroxyalkyldiphenylphosphine oxides 6 and 7 using a combination of sodium borohydride and nickel(II) chloride. Stereospecific elimination of diphenylphosphinic acid from the reduction products using sodium hydride in N,N-dimethylformamide gave homoallylic primary amines 8 and 9 of defined stereochemistry.Keywords
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