Dual Organocatalysis: Asymmetric Allylic–Allylic Alkylation of α,α‐Dicyanoalkenes and Morita–Baylis–Hillman Carbonates

The first highly enantioselective allylic–allylic alkylation of 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 %...

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Published in:Chemistry : a European journal 2009-02, Vol.15 (7), p.1574-1577
Main Authors: Cui, Hai‐Lei, Peng, Jing, Feng, Xin, Du, Wei, Jiang, Kun, Chen, Ying‐Chun
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Alkenes - chemistry
Alkylation
Anthraquinones - chemistry
asymmetric allylic alkylation
Carbonates - chemical synthesis
Carbonates - chemistry
Catalysis
cyclohexenes
Cyclohexenes - chemical synthesis
Cyclohexenes - chemistry
dicyanoalkenes
Ethers - chemistry
Isomerism
Morita–Baylis–Hillman carbonates
Naphthols - chemistry
organocatalysis
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Summary:The first highly enantioselective allylic–allylic alkylation of 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 The first highly enantioselective allylic–allylic alkylation of 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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200802534