The asymmetric Heck and related reactions
Top Cited Papers
- 15 June 2011
- journal article
- review article
- Published by Royal Society of Chemistry (RSC) in Chemical Society Reviews
- Vol. 40 (10), 5122-5150
- https://doi.org/10.1039/c1cs15101k
Abstract
The asymmetric inter- and intramolecular Heck and related reactions are comprehensively reviewed, from their original development to recent advances in terms of substrate scope, reactivity, regio- and enantioselectivity. Their reaction mechanisms/catalytic cycles are discussed in order to understand the concepts underpinning the significant recent developments of these processes. The design and application of new chiral ligands has been pivotal to reaction enhancements and, for each Heck and related process, we classify ligands by the nature of the denticity, chirality and donor atoms involved. In this manner, the continued development of ligand architectural design and application can be more easily monitored for each process. Significant improvements in reaction times, a disadvantage in many Heck reactions, have been addressed through a combination the use of microwave-assisted protocols and ligand design. The asymmetric Fujiwara-Moritani and oxidative boron Heck-type reactions, recent additions to Heck type processes, will also be discussed in this critical review (149 references).This publication has 136 references indexed in Scilit:
- Enantioselective Fujiwara–Moritani Indole and Pyrrole Annulations Catalyzed by Chiral Palladium(II)–NicOx ComplexesEuropean Journal of Organic Chemistry, 2009
- Total Synthesis of the Strychnos Alkaloid (+)-Minfiensine: Tandem Enantioselective Intramolecular Heck−Iminium Ion CyclizationJournal of the American Chemical Society, 2008
- Catalytic Asymmetric Synthesis of Quaternary Carbons Bearing Two Aryl Substituents. Enantioselective Synthesis of 3-Alkyl-3-Aryl Oxindoles by Catalytic Asymmetric Intramolecular Heck ReactionsJournal of the American Chemical Society, 2003
- Preparation of pseudo-C2-symmetric P,S-hybrid ferrocenyl ligand and its application to some asymmetric reactionsJournal of Molecular Catalysis A: Chemical, 2003
- Enantioselective carbon–carbon bond forming reactions using fluorous chiral catalystsJournal of Fluorine Chemistry, 2002
- Synthesis of New Chiral Bidentate (Phosphinophenyl)benzoxazine P,N-LigandsHelvetica Chimica Acta, 1999
- Asymmetric Heck Reactions via Neutral Intermediates: Enhanced Enantioselectivity with Halide Additives Gives Mechanistic InsightsAngewandte Chemie-International Edition, 1997
- Chiral Phosphanyldihydrooxazoles in Asymmetric Catalysis: Enantioselective Heck ReactionsAngewandte Chemie-International Edition, 1996
- Effects of Solvents and Additives in the Asymmetric Heck Reaction of Alkenyl Triflates: Catalytic Asymmetric Synthesis of Decalin Derivatives and Determination of the Absolute Stereochemistry of (+)-VernolepinJournal of the American Chemical Society, 1994
- Asymmetric Heck reaction: a catalytic asymmetric synthesis of the key intermediate for .DELTA.9(12)-capnellene-3.beta.,8.beta.,10.alpha.-triol and .DELTA.9(12)-capnellene-3.beta.,8.beta.,10.alpha.,14-tetrolThe Journal of Organic Chemistry, 1991