Addition of Transiently-Generated Methyl o-Lithiobenzoate to Imines. An Isoindolone Annulation
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (18) , 6205-6211
- https://doi.org/10.1021/jo960582w
Abstract
Addition of phenyllithium to a mixture of an imine, methyl o-iodobenzoate, and BF(3).etherate at -105 degrees C gives good to excellent yields of isoindolones. The transient formation of methyl o-lithiobenzoate is proposed, which is formed by a rapid lithium/iodide exchange reaction of the phenyllithium with methyl o-iodobenzoate in the presence of the imine. The transiently generated anions can then be captured by the BF(3)-activated imines to form the isoindolones in good to high yield. The reactions conditions are sufficiently mild, and selective, to permit functional groups such carbmethoxy and aryl bromide, which could otherwise react with the added PhLi, to be tolerated.Keywords
This publication has 25 references indexed in Scilit:
- Preparations of Secondary Amines and .beta.-Amino Esters via Additions of Grignard and Reformatsky Reagents to Imines and by One-Pot Reactions of Primary Amines, Aldehydes, and GrignardsThe Journal of Organic Chemistry, 1995
- Diastereoface Discrimination in the Addition of Acetylide to a Chiral Aldehyde, Leading to a Synthesis of (+)-Deoxybiotin in Enantiomerically Pure Form Starting from L-CysteineThe Journal of Organic Chemistry, 1994
- Synthesis of 3-substituted and 3,4-disubstituted 3,4-dihydro-1(2H)-isoquinolones by condensation of lithiated N,N-diethyl-o-toluamide with iminesThe Journal of Organic Chemistry, 1987
- Addition of boron trifluoride complexes of organocopper reagentsto aldimines containing α-hydrogensTetrahedron Letters, 1984
- Very high 1,2-asymmetric induction in the reaction of allyl-9-BBN with certain imines. Evidence for a stereoelectronic effect to enhance the Cram selectivityJournal of the American Chemical Society, 1984
- Schiff bases as external and internal electrophiles in reactions of functionalized organolithium reagents. A new route to isoindoline derivatives and 1,2,3,4-tetrahydroisoquinolinesThe Journal of Organic Chemistry, 1981
- Halogen-metal exchange in esters of haloaryl acidsThe Journal of Organic Chemistry, 1976
- Elaboration of bromoarylnitrilesThe Journal of Organic Chemistry, 1976
- Synthesis of isomeric methyl benzoylbenzoates and substituted o-, m-, and p-benzoylbenzoic acidsThe Journal of Organic Chemistry, 1974
- Metalation of N-Methylbenzamide with Excess n-Butyllithium. Condensations with Electrophilic Compounds to Form ortho Derivatives. Cyclizations1The Journal of Organic Chemistry, 1964