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Asymmetric reaction of diethylzinc with aldehydes catalyzed by l-menthopyrazole derivatives

✍ Scribed by Choji Kashima; Kohei Higashide; Yohei Miwa; Yoshihiro Tsukamoto


Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
80 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

N‐Hydroxyalkyl‐1‐menthopyrazoles acted as a chiral catalyst for the diethylzinc (1) addition to aromatic aldehydes, and 1‐aryl‐1‐propanols were afforded enantioselectively. These reactions were carried out optimally in toluene at 40 °C in the presence of 30 mol% of (2′S)‐2‐(2‐phenyl‐2‐hydroxyethyl)‐3‐phenyl‐1‐men‐thopyrazole ((S)‐16d) to afford optically active 1‐aryl‐1‐propanols up to 70% ee (S).


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