Modular Pyridinyl Peptide Ligands in Asymmetric Catalysis: Enantioselective Synthesis of Quaternary Carbon Atoms Through Copper-Catalyzed Allylic Substitutions
- 17 April 2001
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 40 (8) , 1456-1460
- https://doi.org/10.1002/1521-3773(20010417)40:8<1456::aid-anie1456>3.0.co;2-t
Abstract
Highest enantioselectivities so far with dialkylzinc reagents! Quaternary carbon centers are formed enantioselectively through a Cu‐catalyzed allylic substitution reaction that is promoted by pyridinyl peptide‐based ligands in the presence of dialkylzinc reagents (see scheme). The modularity of this new class of chiral ligands is exploited for reactivity and selectivity optimization.This publication has 32 references indexed in Scilit:
- Ti-Catalyzed Regio- and Enantioselective Synthesis of Unsaturated α-Amino Nitriles, Amides, and Acids. Catalyst Identification through Screening of Parallel LibrariesJournal of the American Chemical Society, 2000
- Ti-Catalyzed Enantioselective Addition of Cyanide to Imines. A Practical Synthesis of Optically Pure α-Amino AcidsJournal of the American Chemical Society, 1999
- Search for Chiral Catalysts Through Ligand Diversity: Substrate‐Specific Catalysts and Ligand Screening on Solid PhaseAngewandte Chemie International Edition in English, 1997
- Suche nach chiralen Katalysatoren durch Ligandenvielfalt: substratspezifische Katalysatoren und Screening von Liganden an fester PhaseAngewandte Chemie, 1997
- Chiral Phosphanodihydrooxazoles in Asymmetric Catalysis: Tungsten‐Catalyzed Allylic SubstitutionAngewandte Chemie International Edition in English, 1995
- Chirale Phosphanodihydrooxazole in der asymmetrischen Katalyse: Wolfram‐katalysierte allylische SubstitutionAngewandte Chemie, 1995
- Copper-catalyzed reactions of organotitanium reagents. Highly SN2'- and anti-selective and diastereo- and chemoselective alkylation of allylic chlorides and phosphatesThe Journal of Organic Chemistry, 1991
- Regiocontrol in copper-catalyzed Grignard reactions with allylic substratesJournal of the American Chemical Society, 1990
- Alkylation of allylic derivatives. 11. Copper(I)-catalyzed cross coupling of allylic carboxylates with Grignard reagentsThe Journal of Organic Chemistry, 1986
- Asymmetric Cross-coupling of Organozinc Reagents with Alkenyl Bromides Catalyzed by a Chiral Ferrocenylphosphine-Palladium ComplexBulletin of the Chemical Society of Japan, 1983