Lanthanide (III)-catalyzed enantioselective Diels-Alder reactions. Stereoselective synthesis of both enantiomers by using a single chiral source and a choice of achiral ligands

Journal Article · Wed May 04 00:00:00 EDT 1994 · Journal of the American Chemical Society; (United States)

DOI:https://doi.org/10.1021/ja00088a056· OSTI ID:7019483

Kobayashi, Shu; Ishitani, Haruro ^[1]

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1. Science Univ. of Tokyo (Japan)

In this paper, we disclose a conceptually different approach to obtaining both enantiomers; choice of enatiofacial selectivity by use of the enatiomerically same chiral source and different achiral ligands. Both enantiomers of the Diels-Alder adducts between e-acyl-1,3-oxazolidin-2-ones and cyclopentadiene were prepared by chiral lanthanides(III)-catalyzed reactions using the same chiral source, (R)-(+)-binaphthol. It is noted that the chiral catalysts with reverse enantiofacial selectivities could be prepared by using the same chiral source and a choice of achiral ligands. 14 refs., 3 tabs.

• OSTI ID: 7019483
• Journal Information: Journal of the American Chemical Society; (United States), Journal Name: Journal of the American Chemical Society; (United States) Vol. 116:9; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400201* -- Chemical & Physicochemical Properties
400702 -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
ALCOHOLS
ALKENES
AROMATICS
CATALYSIS
CHARGED PARTICLES
CHEMICAL REACTIONS
CHIRALITY
CYCLOALKENES
CYCLOPENTADIENE
DIELS-ALDER REACTION
DIENES
ENANTIOMORPHS
HYDROCARBONS
HYDROXY COMPOUNDS
IONS
ISOMERS
KETONES
LANTHANUM IONS
LIGANDS
ORGANIC COMPOUNDS
PARTICLE PROPERTIES
POLYENES
SYNTHESIS