Enantioselective Synthesis of Planar-Chiral Carba-Paracyclophanes: Rhodium-Catalyzed [2+2+2] Cycloaddition of Cyclic Diynes with Terminal Monoynes
作者:Tatsuya Araki、Keiichi Noguchi、Ken Tanaka
DOI:10.1002/anie.201300696
日期:2013.5.17
Just ‘plane’ chiral: The high‐yielding and highly enantioselective synthesis of carba[10]–[12]paracyclophanes has been achieved with up to 91 % yield and 93 % ee by using the cationic rhodium(I)/(S,S)‐bdpp‐catalyzed [2+2+2] cycloaddition of cyclic diynes with terminal monoynes under high substrate concentrations. nbd=2,5‐norbornadiene, Ns=p‐nitrobenzenesulfonyl, Ts=4‐toluenesulfonyl.
只是“平面”的手性:卡巴的高产和高度对映选择性合成[10] - [12] paracyclophanes已经与高达91%的收率和93%实现 EE通过使用阳离子铑(I)/(小号,小号)-bdpp催化在高底物浓度下环二炔与末端单炔的[2 + 2 + 2]环加成反应。nbd = 2,5-降冰片二烯,Ns =对-硝基苯磺酰基,Ts = 4-甲苯磺酰基。