Enhanced stereoselectivity in photoelectrocyclization of tropolone ethers via confinement in chiral inductor-modified lyotropic liquid crystals.

作者信息

Lv Feng-Feng, Chen Bin, Wu Li-Zhu, Zhang Li-Ping, Tung Chen-Ho

机构信息

Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.

出版信息

Org Lett. 2008 Aug 21;10(16):3473-6. doi: 10.1021/ol800362c. Epub 2008 Jul 10.

DOI:10.1021/ol800362c

PMID:18613697

Abstract

Photochemistry of tropolone methyl ether ( 1) and optically pure ( S)-tropolone-2-methylbutyl ether ( 4) has been examined in lyotropic liquid crystals (LCs) in the presence of a chiral inductor. LCs significantly enhance the influence of chiral inductors during the photoelectrocyclization of the tropolone ethers. Chiral inductors that lead to 1:1 mixtures of enantiomers or diastereomers in solution give products in up to 40% enantiomeric excess for 1 and 35% diastereomeric excess for 4 in LCs.

摘要