This work was supported by an NSF CAREER Award (CHE-0847273), Vertex Graduate Fellowship, UCI Regents Dissertation Fellowship (B.L.K.), and UROP, NSF-REU, and Allergan Undergraduate Fellowships (N.I.). Charlotte A. Osborne is acknowledged for Table 2, entry 4. Chanel R. Easley is acknowledged for preliminary studies of related transformations. We thank Solvias and Frontier Scientific for donations of chemicals. Dr. John Greaves is acknowledged for mass spectrometry data.
Silver-Catalyzed Allenylation and Enantioselective Propargylation Reactions of Ketones†
Article first published online: 12 MAR 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 16, pages 4414–4417, April 15, 2013
How to Cite
Kohn, B. L., Ichiishi, N. and Jarvo, E. R. (2013), Silver-Catalyzed Allenylation and Enantioselective Propargylation Reactions of Ketones. Angew. Chem. Int. Ed., 52: 4414–4417. doi: 10.1002/anie.201206971
- Issue published online: 11 APR 2013
- Article first published online: 12 MAR 2013
- Manuscript Revised: 5 DEC 2012
- Manuscript Received: 28 AUG 2012
- NSF. Grant Number: CHE-0847273
- asymmetric catalysis;
- tertiary alcohols
More than a silver lining: Certain silver complexes are capable of selective catalysis of either allenylation or asymmetric propargylation reactions of ketones. Ligand-free conditions lead to allenyl alcohols as the major product, whereas ligation with Walphos-8 gives enantioenriched homopropargyl alcohols. This method can be applied to reactions of prochiral diarylketones to provide optically enriched tertiary diaryl alcohols.