Abstract:

    Cyclopropanes are unique three-member rings with their unusual bonding and inherent ring strain making them valuable building blocks in modern organic synthesis[1]. In this work, a Pd-catalyzed diastereo- and enantioselective desymmetric hydrophosphination of 3,3-disubstituted cyclopropenes is described[2]. It allows an efficient, direct and atom-economic access to potentially valuable chiral cyclopropane rings bearing two vicinal carbon stereocenters in high yields with excellent diastereo- and enantioselectivities (up to >98:2 d.r. and 97% ee). Further transformations of these chiral phosphorus-containing three-member rings provide a range of potential applications.

Reference:

[1] (a). Dian, L., and Marek, I. Chem. Rev. 118, 8415-8434. (b). Archambeau, A., Miege, F., Meyer, C., and Cossy, J. Acc. Chem. Res. 48, 1021-1031. (c). Li, P., Zhang, X., and Shi, M. Chem. Commun. 56, 5457-5471.

[2] (a). Lu, Z., Zhang, H., Yang, Z., Ding, N., Meng, L., and Wang, J. ACS Catal. 9, 1457-1463. (b). Yang, Z., and Wang, J. Angew. Chem. Int. Ed. 60, 27288-27292.