A More Comprehensive and Highly Practical Solution to Enantioselective Aldehyde Crotylation
- 12 April 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 133 (17), 6517-6520
- https://doi.org/10.1021/ja200712f
Abstract
The enantioselective crotylation of aldehydes with 1,2-diaminochlorocrotylsilane reagents is effectively catalyzed by Sc(OTf)3. The one significant limitation on the utility of these reagents − substrate scope − has thus been addressed. The net result is the most comprehensive and highly practical method for enantioselective aldehyde crotylation yet advanced.Keywords
This publication has 52 references indexed in Scilit:
- Molecular Biomarker Analyses Using Circulating Tumor CellsPLOS ONE, 2010
- The trifunctional antibody catumaxomab for the treatment of malignant ascites due to epithelial cancer: Results of a prospective randomized phase II/III trialInternational Journal of Cancer, 2010
- Chiral Brønsted Acid-Catalyzed Allylboration of AldehydesJournal of the American Chemical Society, 2010
- An open-label, randomized phase II study of adecatumumab, a fully human anti-EpCAM antibody, as monotherapy in patients with metastatic breast cancerAnnals Of Oncology, 2010
- The Mechanism and an Improved Asymmetric Allylboration of Ketones Catalyzed by Chiral BiphenolsAngewandte Chemie-International Edition, 2009
- anti-Diastereo- and Enantioselective Carbonyl Crotylation from the Alcohol or Aldehyde Oxidation Level Employing a Cyclometallated Iridium Catalyst: α-Methyl Allyl Acetate as a Surrogate to Preformed Crotylmetal ReagentsJournal of the American Chemical Society, 2009
- Tandem Silylformylation−Crotylsilylation/Tamao Oxidation of Internal Alkynes: A Remarkable Example of Generating Complexity from SimplicityOrganic Letters, 2008
- EpCAM expression in normal, non-pathological tissuesFrontiers in Bioscience-Landmark, 2008
- Methylation status of the Ep-CAM promoter region in human breast cancer cell lines and breast cancer tissueCancer Letters, 2006
- Double-Stereodifferentiating Crotylation Reactions with Chiral (E)-Crotylsilanes. Evaluation of a New Approach for the Synthesis of Polypropionate-Derived Natural ProductsJournal of the American Chemical Society, 1996