Stereocontrolled synthesis of homoallylic amines using phosphine oxides and isoxazolines
作者:Susan K. Armstrong、Stuart Warren、Eric W. Collington、Alan Naylor
DOI:10.1016/s0040-4039(00)79895-9
日期:1991.8
Allylic diphenylphosphine oxides (7) undergo stereoselective 1,3-dipolar cycloadditions with nitrile oxides to give Δ2-isoxazolines (8). These may be reduced, also stereoselectively, to δ-amino-β-hydroxyalkyldiphenylphosphine oxides (9). Stereospecific Wittig-Horner type elimination of Ph2PO2− from amino alcohols (9) gives homoallylic amines (10) with controlled double bond geometry.
烯丙基二苯基膦氧化物(7)经历立体选择性1,3-偶极环加成腈氧化物,得到Δ 2个-isoxazolines(8)。这些也可以立体选择性地还原为δ-氨基-β-羟烷基二苯基膦氧化物(9)。博士的立体有择的Wittig-霍纳型消除2 PO 2 -从氨基醇(9)给出高烯丙基胺(10)具有受控的双键的几何形状。