Organocerium Additions to Chiral α,α-Dialkoxy Hydrazones: Asymmetric Synthesis ofN-Protected α-Amino Acetals and α-Amino Aldehydes
- 1 January 1993
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1993 (05) , 359-361
- https://doi.org/10.1055/s-1993-22456
Abstract
A general and selective procedure for the diastereoselective additions of organocerium reagents to chiral α,α-dialkoxy hydrazones has been developed. The best reagent combination involved a 6:1 composition of RMet to CeCl3. Excellent yields and high selectivities were obtained after trapping as the iso-butyl carbamates. Lithiumammonia cleavage of the N-N bond followed by hydrolysis with TMSI afforded the protected α-amino aldehydes.Keywords
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