Tandem Aza[4+2]/allylboration:: A novel multicomponent reaction for the stereocontrolled synthesis of α-hydroxyalkyl piperidine derivatives

被引:52
作者
Tailor, J [1 ]
Hall, DG [1 ]
机构
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
关键词
D O I
10.1021/ol006626b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The alpha -hydroxyalkyl piperidine unit is common to several naturally occurring alkaloids and azasugar analogues. Polysubstituted piperidine derivatives of this kind (3), embodying four stereogenic centers, are formed in just a single operation from the highly stereocontrolled reaction of 4-borono-1-azadienes (1), maleimides, and aldehydes, This novel multicomponent reaction which affords as many as four elements of diversity should prove highly valuable in combinatorial chemistry and natural product synthesis.
引用
收藏
页码:3715 / 3718
页数:4
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