γ-丁内酯的直接催化不对称曼尼希型反应：布朗斯特酸在手性金属催化中的有效性
Direct catalytic asymmetric Mannich-type reactions of gamma-butenolides: effectiveness of Brønsted acid in chiral metal catalysis.
作者信息
Yamaguchi Akitake, Matsunaga Shigeki, Shibasaki Masakatsu
机构信息
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Tokyo, Japan.
出版信息
Org Lett. 2008 Jun 5;10(11):2319-22. doi: 10.1021/ol800756r. Epub 2008 May 7.
Direct catalytic asymmetric Mannich-type reactions of gamma-butenolides are described. A chiral Lewis acid/amine base/Brønsted acid combination was used to catalyze a gamma-addition of gamma-butenolides to N-diphenylphosphinoyl imines, affording the products in up to >99% yield, anti/syn = >97:3, and 84% ee. The use of a catalytic amount of TfOH in addition to La(OTf)3/Me-PyBox/TMEDA was important for improving yield and stereoselectivity.
描述了γ-丁内酯的直接催化不对称曼尼希型反应。使用手性路易斯酸/胺碱/布朗斯特酸组合催化γ-丁内酯与N-二苯基膦酰亚胺的γ-加成反应，产物收率高达>99%，反式/顺式 =>97:3，对映体过量值为84%。除了La(OTf)3/Me-PyBox/TMEDA之外，使用催化量的三氟甲磺酸（TfOH）对于提高收率和立体选择性很重要。
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