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Chiral N,N′-dioxide-iron(II) complexes catalyzed enantioselective oxa-Michael addition of α,β-unsaturated aldehydes

✍ Scribed by Lu Chang; Deju Shang; Junguo Xin; Xiaohua Liu; Xiaoming Feng

Book ID
104095819
Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
179 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

The enantioselective oxa-Michael addition reaction of 1-(4-methoxyphenyl) ethanone oxime to various a,b-unsaturated aldehydes was accomplished by using chiral N,N 0 -dioxide-FeSO 4 Á7H 2 O (1:1) complex.

Aromatic acid was employed as additive to increase the yield of the reaction. The corresponding adducts were obtained in moderate yields with up to 76% ee under mild conditions.

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Enantioselective Michael additions of β-keto esters to α,β-unsaturated carbonyl compounds catalyzed by a chiral biquinoline N,N′-dioxide–scandium trifluoromethanesulfonate complex
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A catalytic, enantioselective Michael addition of b-keto esters to a,b-unsaturated carbonyl compounds was achieved by using a chiral biquinoline N,N 0 -dioxide-scandium trifluoromethanesulfonate complex as a catalyst. The corresponding Michael adducts were obtained in high yields and with enantiosel