Open AccessAn Efficient Approach to Mechanically Planar Chiral Rotaxanes
Author(s) -
Robert J. Bordoli,
Stephen M. Goldup
Publication year - 2014
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja412715m
Subject(s) - chemistry , planar , asymmetry , nanotechnology , combinatorial chemistry , stereochemistry , physics , particle physics , materials science , computer graphics (images) , computer science
We describe the first method for production of mechanically planar chiral rotaxanes in excellent enantiopurity without the use of chiral separation techniques and, for the first time, unambiguously assign the absolute stereochemistry of the products. This proof-of-concept study, which employs a chiral pool sugar as the source of asymmetry and a high-yielding active template reaction for mechanical bond formation, finally opens the door to detailed investigation of these challenging targets.