Lead Tetraacetate Cleavage of Chiral Phenylglycinol Derived Secondary Amines Without Racemization
- 1 July 1993
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 23 (14) , 2055-2064
- https://doi.org/10.1080/00397919308009866
Abstract
Diastereomerically enriched N-(1,1-disubstituted methyl)(2 ‘-hydroxyl’-phenylethyl) amines were oxidatively converted to enantiomerically enriched primary disubstituted methylamines in excellent yields without racemization, using an improved lead tetraacerate (LTA) procedure.Keywords
This publication has 14 references indexed in Scilit:
- An efficient enantiomeric three step synthesis of β-amino acids (esters)Tetrahedron Letters, 1993
- Synthesis of optically active .beta.-lactams by the photolytic reaction of imines with optically active chromium carbene complexes. 2. Synthesis of 1-carbacephalothin and 3-ANA relaysThe Journal of Organic Chemistry, 1992
- Asymmetric conjugate additions to chiral bicyclic lactams. Synthesis of aracemic trans-2,3-disubstituted pyrrolidinesThe Journal of Organic Chemistry, 1992
- 1,2- vs. 1,4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidinesThe Journal of Organic Chemistry, 1992
- Asymmetric synthesis of .gamma.,.gamma.-dialkyl-.gamma.-aminobutyric acid analogs and 2,2-disubstituted pyrrolidines. Control of stereochemistry in aminal ring opening by varying the extent of allylic 1,3 strainJournal of the American Chemical Society, 1991
- Synthesis of chiral .alpha.-alkyl phenethylamines via organometallic addition to chiral 2-aryl-1,3-oxazolidinesThe Journal of Organic Chemistry, 1991
- Enantioselective synthesis of primary amines via Grignard additions to stereogenic N-(.alpha.-phenyl-.beta.-(benzyloxy)ethyl)nitronesThe Journal of Organic Chemistry, 1990
- Synthesis of optically active .beta.-lactams by the photolytic reaction of imines with optically active chromium carbene complexesJournal of the American Chemical Society, 1990
- Chiral purity determination by proton NMR spectroscopy. Novel use of 1,1'-binaphthyl-2,2'-diylphosphoric acidThe Journal of Organic Chemistry, 1989
- Asymmetric synthesis XV : enantiospecific synthesis of (+) and (−) isonitramines from a common chiral intermediateTetrahedron Letters, 1988