Asymmetric Reduction of α-KetoAldoxime O-Ethers
Asymmetric Reduction of α-KetoAldoxime O-Ethers
复制标题
α-酮醛肟O-醚的不对称还原
DOI：
10.1055/s-0030-1258355
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发表时间：
2011
期刊：
影响因子：
--
通讯作者：
M. Pakulski
中科院分区：
文献类型：
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作者：
M. Bosiak;M. Pakulski
以硼烷/恶唑硼烷烷为原料，通过转移加氢和酵母催化不对称还原取代苯乙酮衍生的α-酮醛肟o -甲基、o -苄基和o -三烷基醚。硼烷/恶唑硼烷还原制得相应的α-羟基肟醚、α-羟基胺醚和β-氨基醇，收率为39 ~ 78%，ee为77%。羰基通过RhCl[(R， R)-TsDPEN]（c5 me5）催化甲酸-三乙基胺（c5 me5）的转移加氢选择性还原，也通过酵母的转移加氢选择性还原，分别生成了ee达75%和93%的α-羟基肟醚。
The catalytic asymmetric reduction of α-keto aldoxime O-methyl, O-benzyl,and O-trityl ethers, derived from substituted acetophenones,with borane/oxazaborolidines, by transfer hydrogenation,and with yeast, was studied. The reduction with borane/oxazaborolidinesproduced the corresponding α-hydroxy oxime ethers, α-hydroxyhydroxylamine ethers, and β-amino alcohols in 39-78% yieldsand up to 77% ee. The carbonyl group was selectively reducedby transfer hydrogenation with formic acid-triethyl-aminecatalyzed by RhCl[( R, R)-TsDPEN](C 5 Me 5 ),and also with yeast, producing α-hydroxy oxime ethers,up to 75% ee and 93% ee, respectively.