ORGANOCERIUM ADDITIONS TO CHIRAL ALPHA,ALPHA-DIALKOXY HYDRAZONES - ASYMMETRIC-SYNTHESIS OF N-PROTECTED ALPHA-AMINO ACETALS AND ALPHA-AMINO ALDEHYDES

Authors
DENMARK SE NICAISE O
Citation
Se. Denmark et O. Nicaise, ORGANOCERIUM ADDITIONS TO CHIRAL ALPHA,ALPHA-DIALKOXY HYDRAZONES - ASYMMETRIC-SYNTHESIS OF N-PROTECTED ALPHA-AMINO ACETALS AND ALPHA-AMINO ALDEHYDES, Synlett, (5), 1993, pp. 359-361
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
5
Year of publication
1993
Pages
359 - 361
Database
ISI
SICI code
0936-5214(1993):5<359:OATCAH>2.0.ZU;2-V
Abstract
A general and selective procedure for the diastereoselective additions of organocerium reagents to chiral alpha,alpha-dialkoxy hydrazones ha s been developed. The best reagent combination. involved a 6:1 composi tion of RMet to CeCl3. Excellent yields and high selectivities were ob tained after trapping as the iso-butyl carbamates. Lithium-ammonia cle avage of the N-N bond followed by hydrolysis with TMSI afforded the pr otected alpha-amino aldehydes.