手性螺环双膦氧化物催化的不对称还原-Aldol反应

催化学报 , 2015, (1): 100-105. doi: 10.1016/S1872-2067(14)60241-2

手性螺环双膦氧化物催化的不对称还原-Aldol反应

1.中国科学院上海有机化学研究所金属有机国家重点实验室,上海,200032

2.中国科学院上海有机化学研究所金属有机国家重点实验室,上海,200032

3.中国科学院上海有机化学研究所金属有机国家重点实验室,上海,200032

4.中国科学院上海有机化学研究所金属有机国家重点实验室,上海,200032

基金项目: the National Natural Science Foundation of China(21121062,21232009) the National Basic Research Program of China(2010CB833300) 上海市科学技术委员会 the Chinese Academy of Sciences, and the Science and Technology Commission of Shanghai Municipality. The supporting information of this article is available from the corresponding author.基金来源:国家重点基础研究发展计划(973计划,2010CB833300) 中国科学院国家自然科学基金(21121062,21232009)

关键词：醛 , 不对称催化 , 烯酮 , 路易斯碱 , 还原Aldol反应 , 螺环膦氧化合物

Highly enantio-and diastereoselective reductive aldol reactions catalyzed by chiral spiro bisphosphine oxides

Keywords： Aldehyde , Asymmetric catalysis , Enone , Lewis base , Reductive aldol reaction , Spiro bisphosphine oxide

以螺环膦氧化合物为催化剂及三氯硅氢为还原剂，发展了手性Lewis碱催化的烯酮与醛的不对称还原-Aldol反应。该类催化剂在查耳酮以及类似物与各种醛的不对称还原-Aldol反应中表现出较高的反应活性和良好的立体选择性，以较好的产率(45%-88%)、中等到优秀的非对映选择性(8：92-100：0)以及最高达95%的ee值得到相应的还原Aldol产物。

A spiro bisphosphine oxide (SpinPO) was found to be an efficient chiral Lewis base catalyst in asymmetric reductive aldol reaction of enones and aldehydes in the presence of trichlorosilane as the reductant, affording a variety ofβ‐hydroxyketones in good yields with moderate to high levels of diastereo‐and enantioselectivities.

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