Javier Ortiz, A. Guijarro, M. Yus
Apr 9, 1999
Citations
0
Influential Citations
20
Citations
Journal
Tetrahedron
Abstract
Abstract The reaction of O - tert -butyl- N -(chloromethyl)- N -methyl carbamate ( 1 ) with lithium powder and a catalytic amount of 4,4′-di- tert -butylbiphenyl (DTBB, 2.5 mol %) in the presence of different electrophiles [Me 3 SiCl, i BuCHO, t BuCHO, PhCHO, 4-MeOC 6 H 4 CHO, (CH 2 ) 4 CO, MeCO n Pr, Et 2 CO, MeCO(CH 2 ) 2 CHCH 2 , PhCOMe, PhCO n Bu, Ph 2 CO] in THF at −78°C leads, after hydrolysis with water, to the expected functionalised carbamates 2 . Carbamates 2 derived from carbonyl compounds are deprotected with hydrogen chloride (for aromatic aldehyde or ketone derivatives) or with a mixture of phenol and trimethylsilyl chloride (for aliphatic aldehyde derivatives) giving substituted 1,2-diols 4 .