ON THE USE OF O-METHYLMANDELIC ACID FOR THE ESTABLISHMENT OF ABSOLUTE-CONFIGURATION OF ALPHA-CHIRAL PRIMARY AMINES

Authors
TROST BM BUNT RC PULLEY SR
Citation
Bm. Trost et al., ON THE USE OF O-METHYLMANDELIC ACID FOR THE ESTABLISHMENT OF ABSOLUTE-CONFIGURATION OF ALPHA-CHIRAL PRIMARY AMINES, Journal of organic chemistry, 59(15), 1994, pp. 4202-4205
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
15
Year of publication
1994
Pages
4202 - 4205
Database
ISI
SICI code
0022-3263(1994)59:15<4202:OTUOOA>2.0.ZU;2-L
Abstract
The absolute configuration of alpha-chiral primary amines is correlate d to the relative H-1 NMR shifts (upfield or downfield) observed in th e diastereomeric amides formed from (S)-O-methylmandelic acid. The ami des are easily formed without racemization from either the amine or th e amine salt. A model is described that explains the observed shifts a nd can be used to determine the absolute configuration of unknown alph a-chiral primary amines.