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Asymmetric Aldol Condensation of 1-Naphtol and Pyruvates in the Presence of Lewis Acids Preliminary Communication

✍ Scribed by Oreste Piccolo; Lucio Filippini; Laura Tinucci; Ermanno Valoti; Attilio Citterio

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
209 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Lewis acids catalyze teh condensation of methyl pyruvate and l‐naphtol to give menthyl 2‐hydroxy‐2‐(l‐hydroxy‐2‐naphtyl)propionate in a ratio of up 96:4 in favor of the levorotatory diastereoisomer. Epimerization, at 25°C for five days, occurs on benzylic carbon atom to give a 30:70 mixture enriched with the dextrorotatory isomer.

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