An unusual base-dependent α-alkylation and β-elimination of tert-butyl 2-phenyl-2-oxazoline-4-carboxylate: practical synthesis of (±)-α-alkylserines and tert-butyl benzamidoacrylate

Add time:08/17/2019    Source:sciencedirect.com

Practical synthesis of (±)-α-alkylserines and tert-butyl benzamidoacrylate from tert-butyl 2-phenyl-2-oxazoline-4-carboxylate (6) were developed. The α-alkylation and β-elimination of 6 are dramatically dependent upon base conditions. The phase-transfer catalytic condition bearing solid KOH in toluene gives α-alkylation (up to >99%), and t-BuOK in DMF gives β-elimination (98%).

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