联萘酚磷酸催化环状N-酰基酮亚胺与环状烯酮的不对称曼尼希反应
BINOL Phosphoric Acid-Catalyzed Asymmetric Mannich Reaction of Cyclic N-Acyl Ketimines with Cyclic Enones.
作者信息
Reddy K Nagarjuna, Rao M V Krishna, Sridhar B, Subba Reddy B V
机构信息
Fluoro & Agrochemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India.
Academy of Scientific and Innovative Research (AcSIR), New Delhi, 110025, India.
出版信息
Chem Asian J. 2019 Sep 2;14(17):2958-2965. doi: 10.1002/asia.201900556. Epub 2019 Aug 7.
A highly enantio- and diastereoselective Mannich reaction of cyclic N-acyl ketimines generated in situ from 3-hydroxyisoindolin-1-ones with cyclic enones has been accomplished using a chiral phosphoric acid catalyst to afford the chiral isoindalinone derivatives in high yields with excellent enantioselectivities (upto 97 % ee). This is the first report on the synthesis of chiral isoindolin-1-ones bearing adjacent quaternary and tertiary stereogenic centers.
利用手性磷酸催化剂，实现了由3-羟基异吲哚啉-1-酮原位生成的环状N-酰基酮亚胺与环状烯酮的高度对映和非对映选择性曼尼希反应，以高收率和优异的对映选择性（高达97% ee）得到手性异吲哚啉酮衍生物。这是关于合成具有相邻季碳和叔碳立体中心的手性异吲哚啉-1-酮的首次报道。
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