Michael Addition of Chloroalkyloxazolines to Electron-Poor Alkenes: Synthesis of Heterosubstituted Cyclopropanes
- 23 January 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (4) , 1394-1400
- https://doi.org/10.1021/jo026661r
Abstract
Lithiated 2-(1-chloroethyl)-4,4-dimethyl-2-oxazoline 7 adds to electron-poor alkenyl heterocycles to afford substituted cyclopropanes in excellent yields. A route to chiral nonracemic heterosubstituted cyclopropanes, starting from optically active 2-chloromethyl-2-oxazolines, is highlighted as well.Keywords
This publication has 11 references indexed in Scilit:
- Stereospecific β-Lithiation of Oxazolinyloxiranes: Synthesis of α,β-Epoxy-γ-butyrolactonesOrganic Letters, 2002
- Carbenoid Reactions of 2-Halomethyl-4,6-dimethyl-s-triazinesThe Journal of Organic Chemistry, 2002
- A highly stereoselective synthesis of α,β-unsaturated oxazolinesTetrahedron Letters, 2001
- On the coupling reaction of lithium azaenolates of chiral oxazolines with carbonyl compoundsTetrahedron, 2001
- Ion Pair Acidities and Aggregation of Some Amide and Oxazoline Enolates in THF,The Journal of Organic Chemistry, 1999
- Synthesis of tripyridiniumylpropenyl anions from tripyridiniumylcyclopropanes and -cyclopropenesThe Journal of Organic Chemistry, 1992
- Tripyridylcyclopropene derivatives and their conversion to hexapyridylbenzeneTetrahedron Letters, 1991
- Simple direct titration of organolithium reagents using N-pivaloyl-o-toluidine and/or N-pivaloyl-o-benzylanilineThe Journal of Organic Chemistry, 1989
- Equilibrium acidities in dimethyl sulfoxide solutionAccounts of Chemical Research, 1988
- Novel decarboxylative oxidation of .alpha.-hydroxy-.beta.-keto(or -.beta.-imino) acid salts of mercury(II)The Journal of Organic Chemistry, 1978