Journal of Heterocyclic Chemistry p. 503 - 511 (1998)
Update date:2022-08-02
Topics:
Kashima, Choji
Takahashi, Katsumi
Fukusaka, Kiyoshi
Hosomi, Akira
The conjugate additions of N-(α,β-unsaturated)acylpyrazoles were carried out by the treatment with Grignard reagents in the presence of cuprous halides. The reaction of 2-(α,β-unsaturated)acyl-3-phenyl-l-menthopyrazoles 3a-h occurred in higher chemical yields and with asymmetric inductions on β-position, where the addition of magnesium bromide as a Lewis acid influenced to the yields and the diastereo-selectivities. In the case of α-methylated 2-(α,β-unsaturated)acyl-3-phenyl-l-menthopyrazoles 3i-n, the excellent asymmetric induction on the α-position was also observed through the diastereofacial protonation.
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