Dual organocatalysis: asymmetric allylic-allylic alkylation of alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman carbonates.
The first highly enantioselective allylic-allylic alkylation of alpha,alpha-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.
Cui
Hai-Lei
HL
Key laboratory of Drug-Targeting and Drug Delivery Systems of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, China.
Peng
Jing
J
Feng
Xin
X
Du
Wei
W
Jiang
Kun
K
Chen
Ying-Chun
YC
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D000880:Anthraquinones / Q000737:chemistry*; D002254:Carbonates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D053138:Cyclohexenes / Q000138:chemical synthesis / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D007536:Isomerism; D009284:Naphthols / Q000737:chemistry*
D000475:Alkenes; D000880:Anthraquinones; D002254:Carbonates; D053138:Cyclohexenes; D004987:Ethers; D009284:Naphthols; C538702:hydroquinidine (anthraquinone-1,4-diyl) diether; C412332:1,1'-bi-2-naphthol