Abstract
Vicinally donor-acceptor-substituted 2, 2-dialkoxycylopropanecarboxylic esters 4 are equivalents of 1, 3-zwitterions and have been proved to be valuable synthetic building blocks in organic synthesis. We describe herein the Lewis acid-mediated highly diastereoselective reactions of 4 with (1) esters or acid chlorides to give Claisen-type addition products ; (2) carbonyl compounds to afford γ-lactones ; (3) N-tosylaldimines to give γ-lactams. We also describe the Lewis acid-mediated reactions of 4 with trimethylsilylketene and ketene silyl acetals, affording cyclopentenone derivatives.
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