Enantioselective syntheses of nonracemic benzyl-α-d alcohols via catalytic transfer-hydrogenation with Ru, Os, Rh, and Ir catalysts

被引:30
作者
Faller, JW [1 ]
Lavoie, AR [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
D O I
10.1021/om020058h
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of chiral benzyl-a-d alcohols via the reduction of benialdehyde-a-d derivatives has been investigated with a. series of catalysts that were derived in situ from (1R,2S)- (+)-cis-1-amino-2-indanol and the chloro-bridged dimers of p-cymeneRu, p-cymeneOs, Cp*Rh, or Cp*Ir. An unusual trend was observed in which substrates containing electron-withdrawing substituents led to greater enantioenrichment than those with electron-donating substituents., All four catalyst systems were found to produce benzyl-a-d alcohols with high conversion (>98%). Modest to good enantioselectivites (up to 68% ee) were observed.
引用
收藏
页码:3493 / 3495
页数:3
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