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Studies on the enantioselective catalysis of photochemically promoted transformations: "sensitizing receptors" as chiral catalysts.
J Org Chem. 2003 Jan 10; 68(1):15-21.JO

Abstract

A strategy for the enantioselective catalysis of photomediated reactions in solution is described, involving the use of chiral molecular receptors possessing appendant triplet-sensitizing moieties. Energy transfer is selectively directed to bound substrate as a consequence of the distance dependence of triplet-triplet energy transfer. This effect, which is equivalent to a binding-induced rate enhancement, enables substoichiometric chirality transfer from the receptor template to the substrate, as observed in the intramolecular enone-olefin photo[2 + 2]cycloaddition of a quinolone substrate.

Authors+Show Affiliations

Cauble DF
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.
Lynch V
No affiliation info available
Krische MJ
No affiliation info available

MeSH

BenzophenonesBinding SitesCatalysisCrystallography, X-RayCyclizationHeterocyclic CompoundsLigandsMagnetic Resonance SpectroscopyModels, MolecularMolecular ConformationMolecular StructurePhotochemistryQuinolonesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

12515455

Citation

Cauble, David F., et al. "Studies On the Enantioselective Catalysis of Photochemically Promoted Transformations: "sensitizing Receptors" as Chiral Catalysts." The Journal of Organic Chemistry, vol. 68, no. 1, 2003, pp. 15-21.
Cauble DF, Lynch V, Krische MJ. Studies on the enantioselective catalysis of photochemically promoted transformations: "sensitizing receptors" as chiral catalysts. J Org Chem. 2003;68(1):15-21.
Cauble, D. F., Lynch, V., & Krische, M. J. (2003). Studies on the enantioselective catalysis of photochemically promoted transformations: "sensitizing receptors" as chiral catalysts. The Journal of Organic Chemistry, 68(1), 15-21.
Cauble DF, Lynch V, Krische MJ. Studies On the Enantioselective Catalysis of Photochemically Promoted Transformations: "sensitizing Receptors" as Chiral Catalysts. J Org Chem. 2003 Jan 10;68(1):15-21. PubMed PMID: 12515455.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Studies on the enantioselective catalysis of photochemically promoted transformations: "sensitizing receptors" as chiral catalysts. AU - Cauble,David F, AU - Lynch,Vincent, AU - Krische,Michael J, PY - 2003/1/8/pubmed PY - 2003/6/21/medline PY - 2003/1/8/entrez SP - 15 EP - 21 JF - The Journal of organic chemistry JO - J Org Chem VL - 68 IS - 1 N2 - A strategy for the enantioselective catalysis of photomediated reactions in solution is described, involving the use of chiral molecular receptors possessing appendant triplet-sensitizing moieties. Energy transfer is selectively directed to bound substrate as a consequence of the distance dependence of triplet-triplet energy transfer. This effect, which is equivalent to a binding-induced rate enhancement, enables substoichiometric chirality transfer from the receptor template to the substrate, as observed in the intramolecular enone-olefin photo[2 + 2]cycloaddition of a quinolone substrate. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/12515455/Studies_on_the_enantioselective_catalysis_of_photochemically_promoted_transformations:_"sensitizing_receptors"_as_chiral_catalysts_ DB - PRIME DP - Unbound Medicine ER -