Novel asymmetric oxy-michael addition reaction of the chiral ketones to the achiral gamma--or delta-hydroxy-alpha,beta-unsaturated carbonyl compounds |
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Authors: | Watanabe H Machida K Itoh D Nagatsuka H Kitahara T |
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Affiliation: | Department of Applied Biological Chemistry, The University of Tokyo, Tokyo 113-8657, Japan. ashuten@mail.ecc.u-tokyo.ac.jp |
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Abstract: | A novel asymmetric oxy-Michael addition reaction was developed. In the presence of a catalytic amount of base, chiral ketones 1 and 2, derived from D-glucose and D-fructose, respectively, reacted with omega-hydroxy enones or enoates 3a-e, 17 and 21 to form the hemiacetal-derived alkoxide which underwent stereoselective intramolecular Michael addition to give cyclic acetals. Although the stereoselectivities in the formation of the five-membered acetal rings were modest, six-membered ring formation proceeded with high stereoselectivity and the utility of the reaction was demonstrated by a simple syntheses of natural products. |
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Keywords: | asymmetric reaction oxy‐Michael stereoselective synthesis |
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