Asymmetric construction of functionalized bicyclic imides via [3 + 2] annulation of MBH carbonates catalyzed by dipeptide-based phosphines.
A highly enantioselective [3 + 2] annulation of MBH carbonates and maleimides catalyzed by chiral phosphines has been developed. In the presence of 5 mol % of L-Thr-L-Val-derived phosphine 6, functionalized bicyclic imides were prepared in excellent yields, and with high diastereoselectivities and nearly perfect enantioselectivities.
Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore , 3 Science Drive 3, Republic of Singapore, 117543.
Fangrui
F
Zhong
Guo-Ying
GY
Chen
Xiaoyu
X
Han
Weijun
W
Yao
Yixin
Y
Lu
D002254:Carbonates / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D008301:Maleimides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
D002254:Carbonates; D004151:Dipeptides; D007094:Imides; D008301:Maleimides; D010720:Phosphines