Scientific article
English

High Asymmetric Induction in Lewis Acid-Promoted Intramolecular Ene-Type Reactions: A Diastereo- and Enantioselective Synthesis of (+)-α-Allokainic Acid. Preliminary Communication

Published inHelvetica chimica acta, vol. 63, no. 7, p. 2015-2018
Publication date1980-10-29
First online date2004-10-25
Abstract

The monocyclic amino diacid (+)-α-allokainic acid 1 has been prepared enantioselectively from the ester of cis-β-chloroacrylic acid and (−)-8-phenylmenthol by a series of four synthetic operations in over 15% yield. The crucial step is the intramolecular ‘ene-type’ reaction of the (Z)-diene 4 which on treatment with a mild Lewis acid undergoes a highly accelerated, dia- and enantiostereoselective cyclization to give the pyrrolidines 6 and 7 in a ratio of 95:5 (Scheme 3). Subsequent ester hydrolysis regenerates the auxiliary chiral alcohol. Similar cyclization of the (E)-diene 5 furnished a 15:85 mixture of 6 and 7 showing an efficient reversal of the optical induction by variation of the enoate geometry.

Citation (ISO format)
VON OPPOLZER, Wolfgang, ROBBIANI, Christian, BÄTTIG, Kurt. High Asymmetric Induction in Lewis Acid-Promoted Intramolecular Ene-Type Reactions: A Diastereo- and Enantioselective Synthesis of (+)-α-Allokainic Acid. Preliminary Communication. In: Helvetica chimica acta, 1980, vol. 63, n° 7, p. 2015–2018. doi: 10.1002/hlca.19800630729
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Journal ISSN0018-019X
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