Asymmetric Synthesis of Axially Chiral Biaryls: Inversion of Planar Chirality vs Axial Isomerization and Functionalization at the Side Chain of Biaryl Chromium Complexes
- 29 October 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (24) , 9356-9363
- https://doi.org/10.1021/jo0302307
Abstract
Axially chiral syn-biaryl chromium complexes having a coordinating heteroatom substituent at the benzylic position gave anti-biaryl chromium complexes 5 with inversion of the planar chirality by heating in a nonaromatic solvent, while syn-biaryl chromium complexes with an o-methyl or formyl substituent afforded axially isomerized anti-biaryl chromium complexes under heating in an aromatic solvent. syn-Biaryl and both enantiomeric anti-biaryl chromium complexes with the o-formyl group were stereoselectively prepared from an identical planar chiral arene chromium complex as chiral source. The formyl group of the axially chiral chromium complexes was functionalized by radical cyclization and β-lactam formation, and hetero-Diels−Alder reaction.Keywords
This publication has 13 references indexed in Scilit:
- Planar Chiral (η6-Arene) Ruthenium Cp Complexes in Organic Synthesis: Diastereoselective Complexation of Arene Compounds with Benzylic Alcohol and Its Synthetic Application to Chiral BiarylsOrganometallics, 2003
- Catalytic asymmetric cross-couplingJournal of Organometallic Chemistry, 2002
- Diversity-Oriented Synthesis of Biaryl-Containing Medium Rings Using a One Bead/One Stock Solution PlatformJournal of the American Chemical Society, 2002
- Simultaneous and Stereoselective Construction of Planar and Axial Centers of ChiralityJournal of the American Chemical Society, 2001
- Stereoselective Synthesis of Axially Chiral Natural Products, (−)-Steganone and O,O′-Dimethylkorupensamine A, Utilizing Planar Chiral (Arene)chromium ComplexesTetrahedron, 2000
- Enantioposition-selective arylation of biaryl ditriflates by palladium-catalyzed asymmetric Grignard cross-couplingTetrahedron, 1999
- Stereoselective Synthesis of Both Enantiomers of Axially Chiral Biaryls Utilizing Planar Chiral Tricarbonyl(arene)chromium ComplexesThe Journal of Organic Chemistry, 1996
- N-Lithiomethyl-N,N′N″,N″-tetramethyldiethylene-triamine: The First Alkyllithium Compound which is Monomeric in HydrocarbonsAngewandte Chemie International Edition in English, 1992
- Asymmetric total synthesis of dibenzocyclooctadiene lignans (-)-schizandrin and (-)-isoschizandrin. Structure revision of (+)-isoschizandrinJournal of the American Chemical Society, 1990
- Chiral leaving groups induce asymmetry in syntheses of binaphthyls in nucleophilic aromatic substitution reactionsJournal of the American Chemical Society, 1982