An Efficient Approach to Mechanically Planar Chiral Rotaxanes

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 chir...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-04, Vol.136 (13), p.4817-4820
Main Authors: Bordoli, Robert J, Goldup, Stephen M
Format: Article
Language:English
Subjects:
Asymmetry
Bonding
Communication
Pools
Rotaxanes
Separation
Stereochemistry
Sugars
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja412715m