Atropisomer

Atropisomers are stereoisomers arising because of hindered rotation about a single bond, where energy differences due to steric strain or other contributors create a barrier to rotation that is high enough to allow for isolation of individual conformers.^[1]^[2] They occur naturally and are important in pharmaceutical design.^[3] When the substituents are achiral, these conformers are enantiomers (atropoenantiomers), showing axial chirality; otherwise they are diastereomers (atropodiastereomers).^[1]

^ ^a ^b Bringmann, Gerhard; Mortimer, Anne J. Price; Keller, Paul A.; Gresser, Mary J.; Garner, James; Breuning, Matthias (2005). "Atroposelective Synthesis of Axially Chiral Biaryl Compounds". Angewandte Chemie International Edition. 44 (34): 5384–5427. doi:10.1002/anie.200462661. PMID 16116589.
^ Anslyn, Eric V.; Dougherty, Dennis A. (2006). Modern physical organic chemistry. Mill Valley, CA: University Science Books. ISBN 1-891389-31-9. OCLC 55600610.
^ Clayden, Jonathan; Moran, Wesley J.; Edwards, Paul J.; LaPlante, Steven R. (2009). "The Challenge of Atropisomerism in Drug Discovery". Angew. Chem. Int. Ed. 48 (35): 6398–6401. doi:10.1002/anie.200901719. ISSN 1433-7851. PMID 19637174.

[Bringman2005-1] Bringmann, Gerhard; Mortimer, Anne J. Price; Keller, Paul A.; Gresser, Mary J.; Garner, James; Breuning, Matthias (2005). "Atroposelective Synthesis of Axially Chiral Biaryl Compounds". Angewandte Chemie International Edition. 44 (34): 5384–5427. doi:10.1002/anie.200462661. PMID 16116589.

[Anslyn-2] Anslyn, Eric V.; Dougherty, Dennis A. (2006). Modern physical organic chemistry. Mill Valley, CA: University Science Books. ISBN 1-891389-31-9. OCLC 55600610.

[Clayden_2009-3] Clayden, Jonathan; Moran, Wesley J.; Edwards, Paul J.; LaPlante, Steven R. (2009). "The Challenge of Atropisomerism in Drug Discovery". Angew. Chem. Int. Ed. 48 (35): 6398–6401. doi:10.1002/anie.200901719. ISSN 1433-7851. PMID 19637174.

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