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

✍ Scribed by Hai-Lei Cui; Jing Peng; Xin Feng; Wei Du; Kun Jiang; Ying-Chun Chen

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 240 KB
• Volume: 15
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200802534

✦ Synopsis

Abstract

The first highly enantioselective allylic–allylic alkylation of α,α‐dicyanoalkenes and Morita–Baylis–Hillman carbonates by dual catalysis of (DHQD)~2~AQN 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)~2~AQN=hydroquinidine (anthraquinone‐1,4‐diyl) diether, (S)‐BINOL =(S)‐(−)‐1,1′‐bi‐2‐naphthol.magnified image

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