Enantioselective Nucleophilic Catalysis with “Planar-Chiral” Heterocycles
Top Cited Papers
- 18 March 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in Accounts of Chemical Research
- Vol. 33 (6) , 412-420
- https://doi.org/10.1021/ar990077w
Abstract
Although Lewis bases (e.g., tertiary phosphines, tertiary amines, and pyridines) serve as nucleophilic catalysts for a wide array of reactions, there have been relatively few reports of enantioselective nucleophilic catalysts. In this Account, we describe the design and synthesis of a new family of chiral nucleophilic catalysts, specifically, planar-chiral heterocycles. These complexes provide good levels of enantiomeric excess in the addition of alcohols to ketenes, the rearrangement of O-acylated azlactones, and the kinetic resolution of secondary alcohols.Keywords
This publication has 18 references indexed in Scilit:
- Enantioselective Addition of Alcohols to Ketenes Catalyzed by a Planar-Chiral Azaferrocene: Catalytic Asymmetric Synthesis of Arylpropionic AcidsJournal of the American Chemical Society, 1999
- Enantioselective Construction of Quaternary Stereocenters: Rearrangements of O-Acylated Azlactones Catalyzed by a Planar-Chiral Derivative of 4-(Pyrrolidino)pyridineJournal of the American Chemical Society, 1998
- Effective Kinetic Resolution of Secondary Alcohols with a Planar−Chiral Analogue of 4-(Dimethylamino)pyridine. Use of the Fe(C5Ph5) Group in Asymmetric CatalysisJournal of the American Chemical Society, 1997
- Chiral π-Complexes of Heterocycles with Transition Metals: A Versatile New Family of Nucleophilic CatalystsThe Journal of Organic Chemistry, 1996
- Secalonic acids D and F are toxic metabolites of Aspergillus aculeatusThe Journal of Organic Chemistry, 1977
- Optically Active 2‐MethylazaferroceneAngewandte Chemie International Edition in English, 1969
- Organische Katalysatoren. LXXI Asymmetrische Synthesen mit Ketenen. IV. Zusammenhänge zwischen dem räumlichen Bau einiger alkaloidartiger Katalysatoren und ihren stereospezifischen Wirkungen bei asymmetrischen EstersynthesenJournal für Praktische Chemie, 1964
- Asymmetrische Synthesen mit Ketenen, III. Über den Lösungsmitteleinfluß auf den sterischen Ablauf zweier asymmetrischer AmidsynthesenEuropean Journal of Inorganic Chemistry, 1963
- Über Reaktionen an der Carbonamidgruppe, VII. N‐Nitroso‐N‐acyl‐Derivate des Cyclohexylamins und des 1.4‐Diamino‐cyclohexansEuropean Journal of Organic Chemistry, 1960
- Ueber quantitative Esterbildung und Bestimmung von Alkoholen resp. PhenolenEuropean Journal of Inorganic Chemistry, 1901