Organic synthesis using haloboration reaction. Part 7. A stereospecific synthesis of (Z)-. delta.-halo-. gamma.,. delta.-unsaturated ketones via haloboration reaction of …

…, H Serizawa, S Hara, A Suzuki

文献索引：Satoh, Yoshitaka; Serizawa, Hirokazu; Hara, Shoji; Suzuki, Akira Journal of the American Chemical Society, 1985 , vol. 107, # 18 p. 5225 - 5228

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被引用次数: 35

摘要

Abstract: Michael-type reactions of (Z)-@-bromo-and iodoalkenyl-9-borabicyclo [3.3. llnonanes (9, readily available by haloboration of 1-alkynes, with acyclic a,@-unsaturated ketones (2) in a nonpolar solvent under Lewis acidic conditions are presented. The products,(Z)-&halo-y, b-unsaturated ketones (6), are obtained in stereochemically pure form (> 98%). Since the haloalkenylboranes (5) are prepared in situ from haloboranes (4) and ...