Catalytic Asymmetric Conjugate Allylation of Coumarins
Authors:
- 21 June 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 13 (15) , 3814-3817
Abstract
A catalytic asymmetric conjugate allylation was successfully developed to synthesize potential pharmacologically active 4-allyl-2-oxochroman skeletons. A dual activation strategy was employed by using N,N′-dioxide-Yb(OTf)3 to activate coumarins and using (CuOTf)2•C7H8 to activate tetraallyltin via transmetalation, respectively. Good yields and enantioselectivities were obtained under mild conditions.Keywords
This publication has 56 references indexed in Scilit:
- Catalytic Enantioselective Conjugate Allylation of Unsaturated Methylidene KetonesOrganic Letters, 2011
- Asymmetric Ni-Catalyzed Conjugate Allylation of Activated EnonesJournal of the American Chemical Society, 2008
- Highly Enantioselective Allylation of Aromatic α‐Keto Phosphonates Catalyzed by Chiral N,N′‐Dioxide‐Indium(III) ComplexesAdvanced Synthesis & Catalysis, 2008
- Indium and zinc-mediated Barbier-type addition reaction of 2,3-allenals with allyl bromide: an efficient synthesis of 1,5,6-alkatrien-4-olsOrganic & Biomolecular Chemistry, 2008
- Highly Concentrated Catalytic Asymmetric Allylation of KetonesOrganic Letters, 2007
- Cuprous Chloride Accelerated Stille Reactions. A General and Effective Coupling System for Sterically Congested Substrates and for Enantioselective SynthesisJournal of the American Chemical Society, 1999
- Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potentialGeneral Pharmacology: The Vascular System, 1996
- Acyloxybenzyl halides, inhibitors of elastasesBiochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology, 1991
- Structure-activity correlation of flavonoids for inhibition of bovine lens aldose reductase.Chemical and Pharmaceutical Bulletin, 1989
- A general allylation procedure using trimethylallylsilane and fluoride catalysisThe Journal of Organic Chemistry, 1986