HETEROCYCLIZATIONS OF N-BOC DERIVATIVES OF BETA-AMINO ALCOHOLS AND THIO ANALOGS - AN UNUSUAL CASE OF THE THORPE-INGOLD EFFECT

Authors
AGAMI C COUTY F HAMON L VENIER O
Citation
C. Agami et al., HETEROCYCLIZATIONS OF N-BOC DERIVATIVES OF BETA-AMINO ALCOHOLS AND THIO ANALOGS - AN UNUSUAL CASE OF THE THORPE-INGOLD EFFECT, Bulletin de la Societe chimique de France, 132(8), 1995, pp. 808-814
Citations number
47
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
132
Issue
8
Year of publication
1995
Pages
808 - 814
Database
ISI
SICI code
0037-8968(1995)132:8<808:HONDOB>2.0.ZU;2-V
Abstract
Enantiopure oxazolidin-2-ones were synthesized from chiral N-Boc beta- aminoalcohols which underwent a cyclization upon treatment with tosyl chloride. This reaction was strongly accelerated in the case of carbam ates derived from N-methylated amines. A similar heterocyclization was observed with dithiocarbamates, ie sulfur analogs of carbamates. The rate enhancement due to the nitrogen substitution was studied by AM1 c alculations.