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Synlett 1993; 1993(5): 359-361
DOI: 10.1055/s-1993-22456
DOI: 10.1055/s-1993-22456
letter
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Organocerium Additions to Chiral α,α-Dialkoxy Hydrazones: Asymmetric Synthesis of N-Protected α-Amino Acetals and α-Amino Aldehydes
Further Information
Publication History
Publication Date:
19 March 2002 (online)
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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.