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Kinetically controlled Ferrier rearrangement of 3-O-mesyl-D-glycal derivatives
Yuhya Watanabe1, Tsubasa Itoh, Tohru Sakakibara
1Graduate School of Integrated Science, Yokohama City University, Kanazawa-ku, Yokohama, Japan.
Abstract:
The Ferrier rearrangement, which is widely used in carbohydrate chemistry, is generally performed under acidic conditions to give an alpha anomer with high stereoselectivity. We have found that 3-O-mesyl-D-glycals 2-4 were smoothly reacted with alcohols in the presence of triethylamine. The present reaction was shown to proceed under kinetic control to give approximately 1.3:1.0 mixture of alpha and beta anomers, indicating that a kinetic anomeric effect does not operate.
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