An Organocatalytic, δ‐Regioselective, Diastereoselective, and Enantioselective Nucleophilic Substitution of Cyclic Morita–Baylis–Hillman Alcohols with N‐Boc‐3‐benzyl‐2‐oxindoles
An Organocatalytic, δ‐Regioselective, Diastereoselective, and Enantioselective Nucleophilic Substitution of Cyclic Morita–Baylis–Hillman Alcohols with N‐Boc‐3‐benzyl‐2‐oxindoles
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DOI：
10.1002/ejoc.201201461
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发表时间：
2013-04
影响因子：
2.8
通讯作者：
Z. Qiao;N. Zhong;Tao Zhang;Li Liu;Dong Wang;Yong-Jun Chen
中科院分区：
文献类型：
--
作者：
Z. Qiao;N. Zhong;Tao Zhang;Li Liu;Dong Wang;Yong-Jun Chen
开发了一种直接不对称取代反应，用于环状 Morita-Baylis-Hillman 醇与 3-benzyl-2-oxindoles 的反应，该反应由生物碱衍生的伯胺与三氟乙酸结合催化。获得了具有邻位手性季碳和叔碳中心的不寻常的 δ-产物作为主要产物，产率高达 73%，具有优异的非对映选择性（高达 99:1）和对映选择性（高达 98% ee）。
A direct asymmetric substitution was developed for the reaction of cyclic Morita–Baylis–Hillman alcohols with 3-benzyl-2-oxindoles that are catalyzed by a primary amine derived from alkaloids in combination with trifluoroacetic acid. The unusual δ-products with vicinal chiral quaternary and tertiary carbon centers were obtained as the major products in yields up to 73 % with excellent diastereoselectivities (up to 99:1) and enantioselectivities (up to 98 % ee).