ISOCYANATES .4. CONVENIENT PHOSGENE-FREE METHOD FOR THE SYNTHESIS ANDDERIVATIZATION OF ENANTIOPURE ALPHA-ISOCYANATO CARBOXYLIC-ACID ESTERS

Authors
KNOLKER HJ BRAXMEIER T
Citation
Hj. Knolker et T. Braxmeier, ISOCYANATES .4. CONVENIENT PHOSGENE-FREE METHOD FOR THE SYNTHESIS ANDDERIVATIZATION OF ENANTIOPURE ALPHA-ISOCYANATO CARBOXYLIC-ACID ESTERS, Synlett, (8), 1997, pp. 925
Citations number
22
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
8
Year of publication
1997
Database
ISI
SICI code
0936-5214(1997):8<925:I.CPMF>2.0.ZU;2-Y
Abstract
A novel phosgene-free procedure for the synthesis of alpha-isocyanato carboxylic acid esters starting from alpha-amino acid esters has been achieved. The isocyanates are obtained enantiomerically pure (> 99% ee l by a DMAP-catalyzed isocyanation with di-tert-butyl dicarbonate, whi ch proceeds in 10 min at room temperature. In situ derivatization of t he isocyanates by reaction with amines and alcohols affords the corres ponding enantiopure ureas and carbamates.