Synthesis of diastereometrically pure cubane-like photodimers from 2,4-pentanediyl-bis-2-naphthoates

Su-Fang Cheng; Bin Chen; Xiu-Jie Yang; Lin Luo; Li-Ping Zhang; Li-Zhu Wu; Chen-Ho Tung

doi:10.1039/c3pp50326g

Synthesis of diastereometrically pure cubane-like photodimers from 2,4-pentanediyl-bis-2-naphthoates

Photochem Photobiol Sci. 2014 Feb;13(2):261-5. doi: 10.1039/c3pp50326g.

Authors

Su-Fang Cheng¹, Bin Chen, Xiu-Jie Yang, Lin Luo, Li-Ping Zhang, Li-Zhu Wu, Chen-Ho Tung

Affiliation

¹ Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190, China. chtung@mail.ipc.ac.cn lzwu@mail.ipc.ac.cn.

PMID: 24178437
DOI: 10.1039/c3pp50326g

Abstract

Irradiation of (2R,4R)-(-)- and (2S,4S)-(+)-2,4-pentanediyl-bis-2-naphthoates (1R and 1S, respectively) in organic solutions exclusively results in cubane-like anti(HH) photodimers in 100% yield. Asymmetric induction with 100% diastereometric excess (de) has been achieved and the absolute configuration of the yielded diastereomers has been established. Moreover, irradiation of (2R,4S)-2,4-pentanediyl-bis-2-naphthoate (1M) gives cubane-like syn(HH) photodimers in 100% yield.