Abstract
The highly enantioselective NHC-catalyzed [3+2] annulation reaction with α,β-alkynals and α-ketoesters has been developed. A new mode of cooperative catalysis involving the combination of a chiral Brønsted acid and a C1-symmetric biaryl saturated-imidazolium precatalyst was required to generate the desired γ-crotonolactones in high yields and levels of enantioselectivity.
Original language | English (US) |
---|---|
Pages (from-to) | 7594-7598 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 53 |
Issue number | 29 |
DOIs | |
State | Published - Jul 14 2014 |
Keywords
- N-heterocyclic carbene
- annulation
- asymmetric synthesis
- cooperative catalysis
- synthetic methods
ASJC Scopus subject areas
- General Chemistry
- Catalysis
Fingerprint
Dive into the research topics of 'A cooperative N-heterocyclic carbene/chiral phosphate catalysis system for allenolate annulations'. Together they form a unique fingerprint.Datasets
-
CCDC 974554: Experimental Crystal Structure Determination
Lee, A. (Creator) & Scheidt, K. A. (Creator), Cambridge Crystallographic Data Centre, 2014
DOI: 10.5517/cc11q373, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc11q373&sid=DataCite
Dataset
-
CCDC 957094: Experimental Crystal Structure Determination
Lee, A. (Creator) & Scheidt, K. A. (Creator), Cambridge Crystallographic Data Centre, 2014
DOI: 10.5517/cc113y03, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc113y03&sid=DataCite
Dataset