Abstract
2-Alkyl-2-methyl-3-butenenitriles which have an asymmetric quaternary carbon atom at the a-position were obtained from 2-methyl-2-butenal SAMP hydrazone in good enantiomeric excesses (e.e. = 73-95 %). This shows that diastereoselective alkylation occurred at the a-position and the a,b-unsaturated double bond migrated to b,g. The absolute configuration of 2-benzyl-2-methyl-3-butenenitrile was determined as R by derivatization and comparison of optical rotation.
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