Stereoselective desymmetrisation of prochiral alpha,alpha-dicyanoalkenes via domino Michael-Michael addition reactions.
The desymmetrisation of prochiral alpha,alpha-dicyanoalkenes via tandem Michael-Michael addition reactions with alpha,beta-unsaturated ketones catalysed by 9-amino-9-deoxyepicinchona alkaloids was investigated, from which bicyclic products bearing four stereogenic centers were afforded in a single operation with high stereoselectivities (>99% de, up to >99.5% ee).
Kang
Tai-Ran
TR
Key Laboratory of Drug Targeting and Drug Delivery Systems of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, China.
Xie
Jian-Wu
JW
Du
Wei
W
Feng
Xin
X
Chen
Ying-Chun
YC
D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D003516:Cycloparaffins / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
D002930:Cinchona Alkaloids; D003516:Cycloparaffins; D007659:Ketones; D009570:Nitriles; C412619:1,3-dicyanobenzene