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An efficient approach to mechanically planar chiral rotaxanes.

ABSTRACT: 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.

SUBMITTER: Bordoli RJ

PROVIDER: S-EPMC3977585 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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An efficient approach to mechanically planar chiral rotaxanes.

Bordoli Robert J RJ Goldup Stephen M SM

Journal of the American Chemical Society 20140318 13

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. ...[more]

PMID: 24559064

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