Easily accessible C2-symmetric chiral bicyclo[3.3.0] dienes as ligands for rhodium-catalyzed asymmetric 1,4-addition.
The synthesis of a new type of C(2)-symmetric chiral diene ligands with a nonbridged bicyclic [3.3.0] backbone was successfully introduced. Using highly efficient lipase-catalyzed transesterification and Suzuki-coupling strategies, a broad family of enantiopure 3,6-disubstituted bicyclo[3.3.0] dienes with different electronic and steric properties could be easily prepared. The application of these new diene ligands in the Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to alpha,beta-unsaturated carbonyl compounds have been examined, and excellent enantioselectivities (up to 98 % ee) as well as good yields are achieved under very mild reaction conditions at room temperature.
Feng
Chen-Guo
CG
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, China.
Wang
Zhi-Qian
ZQ
Tian
Ping
P
Xu
Ming-Hua
MH
Lin
Guo-Qiang
GQ
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D008024:Ligands; D002244:Carbon; D012238:Rhodium