Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes

Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes
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DOI:
10.1021/ol0162116
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发表时间:
2001-07-26
期刊:
影响因子:
5.2
通讯作者:
Nguyen, ST
Nguyen, ST
中科院分区:
化学1区
文献类型:
--
作者:
Campbell, EJ;Zhou, HY;Nguyen, ST

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使用简单的铝预催化剂成功地进行了催化MPV还原。使用(PrOH)-Pr-i作为还原剂,将烷基铝试剂转化为低聚集铝醇盐,其对于几种羰基底物的MPV还原具有高活性,产率(50-99%)。在(PrOH)-Pr-i还原2-甲基环己酮(cis/trans = 20/80)中实现了高度的顺/反选择性。当使用手性氢化物源还原2氯苯乙酮时,观察到高的对映选择性(68- 80%ee)。
[GRAPHICS]Catalytic MPV reduction was successfully carried out using simple aluminum precatalysts, Alkylaluminum reagents were converted to a low-aggregation aluminum alkoxide that was highly active for the MPV reduction of several carbonyl substrates in high yield (50-99%) using (PrOH)-Pr-i as the reducing agent. A high degree of cis/trans selectivity was achieved in the reduction of 2-methylcyclohexanone (cis/trans = 20/80) by (PrOH)-Pr-i. When chiral hydride sources were utilized in the reduction of 2 chloroacetophenone, high enantioselectivity (68-80% ee) was observed.