Induction of molecular asymmetry by a remote chiral group

Patrick Linnane, Nicholas Magnus and Philip Magnus
Additional contact information
Patrick Linnane: University of Texas at Austin
Nicholas Magnus: University of Texas at Austin
Philip Magnus: University of Texas at Austin

Nature, 1997, vol. 385, issue 6619, 799-801

Abstract: Abstract Conventional methods of asymmetric synthesis of organic compounds involve the use of either chiral catalysts or stoichiometric amounts of chiral substrates. Invariably, the reacting components must be in close proximity to the entity that introduces chirality1,2. But supramolecular chemistry3–5 has shown that stereochemical information can be transmitted through greater distances than are commonly involved in asymmetric syntheses. Here we show that chiral information can be transmitted with remarkable selectivity through as many as nine achiral connecting atoms to give predominantly one diastereomer of a possible four. This contrasts with the general expectation6 that a decrease in selectivity would result from an increase in the separation of the chirality-inducing substituent and the reaction site. This ability to convey molecular asymmetry over larger distances should provide access to new chiral molecules that would be difficult to make by conventional methods.

Date: 1997
References: Add references at CitEc
Citations: View citations in EconPapers (1)

Downloads: (external link)
https://www.nature.com/articles/385799a0 Abstract (text/html)
Access to the full text of the articles in this series is restricted.

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:nature:v:385:y:1997:i:6619:d:10.1038_385799a0

Ordering information: This journal article can be ordered from
https://www.nature.com/

DOI: 10.1038/385799a0

Access Statistics for this article

Nature is currently edited by Magdalena Skipper

More articles in Nature from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().