Dual Organocatalysis: Asymmetric Allylic-Allylic Alkylation of α,α-Dicyanoalkenes and Morita-Baylis-Hillman Carbonates
Dual Organocatalysis: Asymmetric Allylic-Allylic Alkylation of α,α-Dicyanoalkenes and Morita-Baylis-Hillman Carbonates
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DOI：
10.1002/chem.200802534
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发表时间：
2009-01-01
影响因子：
4.3
通讯作者：
Chen, Ying-Chun
中科院分区：
文献类型：
--
作者：
Cui, Hai-Lei;Peng, Jing;Chen, Ying-Chun
研究了α，α-二氰基烯烃和Morita-Baylis-Hillman碳酸酯在（DHQD）2AQN和（S）-BINOL双重催化下的首次高对映选择性烯丙基-烯丙基烷基化反应。对于宽范围的底物（d.r. > 99：1，高达99%ee）。多官能烯丙基产物可以有效地转化为一系列复杂的手性环状骨架。EWG=吸电子基团，（DHQD）2AQN=氢化奎尼丁（蒽醌-1，4-二基）二醚，（S）-BINOL =（S）-（−）-1，1 ′-联-2-萘酚。
The first highly enantioselective allylic–allylic alkylationof α,α‐dicyanoalkenes and Morita–Baylis–Hillman carbonates by dual catalysis of (DHQD)2AQN and (S)‐BINOL has been investigated. Excellent stereoselectivities have been achieved for a broad spectrum of substrates (d.r. > 99:1, up to 99 %ee). The multifunctional allylic products could be efficiently converted to a range of complex chiral cyclic frameworks. EWG=electron‐withdrawing group, (DHQD)2AQN=hydroquinidine (anthraquinone‐1,4‐diyl) diether, (S)‐BINOL =(S)‐(−)‐1,1′‐bi‐2‐naphthol.No Abstract