Enantioselective Iodolactonization Catalyzed by Chiral Quaternary Ammonium Salts Derived from Cinchonidine
- 18 March 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (8), 2874-2876
- https://doi.org/10.1021/jo035719e
Abstract
Chiral quaternary ammonium salts derived from cinchonidine have been applied to catalyze the stereoselective iodolactonizations of trans-5-aryl-4-pentenoic acids leading to a mixture of two regioselectively iodolactonized products with fair to excellent yield (37−98%) and moderate enantioselectivity (exo = 42.0% ee, endo = 31.0% ee) under mild conditions. This work is the first example of asymmetric iodolactonization reaction in the presence of less than a stoichiometric amount of chiral reagent.Keywords
This publication has 9 references indexed in Scilit:
- Enantiospecific Synthesis of the Phospholipase A2 Inhibitor (−)-Cinatrin BThe Journal of Organic Chemistry, 2002
- Reagent-Controlled Stereoselective IodolactonizationsOrganic Letters, 2001
- Asymmetric Phase-Transfer CatalysisAngewandte Chemie-International Edition, 1999
- The first reagent-controlled asymmetric halolactonizations. Dihydroquinidine-halogen complexes as chiral sources of positive halogen ionCanadian Journal of Chemistry, 1998
- Macrocyclic Polyethers as Enolate Activators in Base-Catalyzed Phase-Transfer ReactionsThe Journal of Organic Chemistry, 1998
- A new safety-catch peptide-resin linkage for the direct release of peptides into aqueous buffersTetrahedron Letters, 1994
- Doubly Diastereoselective Iodolactonizations: Olefin and Face Selectivity in Nona-2,7-diene-5-carboxylic Acid CyclizationsThe Journal of Organic Chemistry, 1994
- Stereocontrolled cyclofunctionalizations of double bonds through heterocyclic intermediatesTetrahedron, 1990
- Synthesis and synthetic utility of halolactonesChemical Society Reviews, 1979