An Enantioselective Route to α-Methyl Carboxylic Acids via Metal and Enzyme Catalysis
- 23 October 2007
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (24) , 5095-5098
- https://doi.org/10.1021/ol702261t
Abstract
Dynamic kinetic resolution of allylic alcohols to allylic acetates followed by copper-catalyzed allylic substitution gave alkenes in high yields and high optical purity. Subsequent oxidative C-C double bond cleavage afforded pharmaceutically important alpha-methyl substituted carboxylic acids in high ee.Keywords
This publication has 30 references indexed in Scilit:
- (S)‐Selective Kinetic Resolution and Chemoenzymatic Dynamic Kinetic Resolution of Secondary AlcoholsChemistry – A European Journal, 2005
- (S)-Selective Dynamic Kinetic Resolution of Secondary Alcohols by the Combination of Subtilisin and an Aminocyclopentadienylruthenium Complex as the CatalystsJournal of the American Chemical Society, 2003
- Regiocontrol in Copper-Catalyzed Cross Coupling of Allylic Chlorides with Aryl Grignard ReagentsThe Journal of Organic Chemistry, 1994
- A dual regiocontrol in the copper-catalysed Grignard reaction with primary allylic acetatesJournal of the Chemical Society, Chemical Communications, 1987
- Alkylation of allylic derivatives. 7. Stereochemistry of alkylation of the isomeric trans-.alpha.,.gamma.-methyl(phenyl)allyl acetates with lithium dialkylcuprates and alkylcyanocupratesThe Journal of Organic Chemistry, 1983
- Alkylation of allylic derivatives. 6. Regiochemistry of alkylation of allylic acetates with dialkylcupratesThe Journal of Organic Chemistry, 1983
- Alkylation of allylic derivatives. 5. Loss of double-bond configuration associated with .alpha.-alkylation of allylic carboxylates with dialkylcupratesThe Journal of Organic Chemistry, 1983
- Alkylation of allylic derivatives. Regio- and stereochemistry of alkylation of allylic alcohols by the Murahashi methodThe Journal of Organic Chemistry, 1981
- Chirality transfer in acyclic systems via organocopper chemistryThe Journal of Organic Chemistry, 1980
- The stereochemistry of conversion of allylic esters to olefins with lithium dialkylcupratesJournal of the American Chemical Society, 1976