jo061541v_si_001.cif (16.95 kB)
Efficient Asymmetric Synthesis of Novel Gastrin Receptor Antagonist AG-041R via Highly Stereoselective Alkylation of Oxindole Enolates
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posted on 2006-10-27, 00:00 authored by Takashi Emura, Toru Esaki, Kazutaka Tachibana, Makoto ShimizuAn efficient method for asymmetric synthesis of the potent Gastrin/CCK-B receptor antagonist AG-041R was developed. Core oxindole stereochemistry was established by asymmetric alkylation of oxindole
enolates with bromoacetic acid esters, using l-menthol as a chiral auxiliary. The key alkylation reaction
of the oxindole enolates generated tetrasubstituted chiral intermediates with high diastereoselectivity.
The stereoselective alkylation reactions are described in detail.