Asymmetric direct vinylogous Michael reaction of activated alkenes to nitroolefins catalyzed by modified cinchona alkaloids.
[reaction: see text] The first organocatalytic and asymmetric direct vinylogous Michael reaction that employs the electron-deficient vinyl malononitriles as the nucleophilic species has been reported. The novel transformations exhibit exclusive gamma-selectivity and high diastereo- and enantioselectivity in the addition to nitroolefins, which give the multifunctional products with two vicinal chiral centers.
Xue
Dong
D
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
Chen
Ying-Chun
YC
Wang
Qi-Wei
QW
Cun
Ling-Feng
LF
Zhu
Jin
J
Deng
Jin-Gen
JG
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D000475:Alkenes; D002930:Cinchona Alkaloids; D009574:Nitro Compounds; D014753:Vinyl Compounds