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Cyclopropane derivatives 1a-c, 16, and 20 were prepared from a rhodium-catalyzed carbene insertion reaction of the corresponding diazocompound with allyl tert-butyldiphenylsilane.
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note
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The assignment of the relative stereochemistry of 17-19, 21, and 22 by NOE measurements was difficult because of the crowded nature of the spectrum. Efforts are being made to secure the same through derivatization and crystal structure illucidation.
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2O (2 x 5 mL). The combined organic extracts were washed with brine, dried, and concentrated. Purification of the residue by silica gel column chromatography (EtOAc/hexanes) furnished the pure product(s). The separation of the cis- and trans-isomers was achieved by radial chromatography over silica gel (EtOAc/hexanes).
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2O (2 x 5 mL). The combined organic extracts were washed with brine, dried, and concentrated. Purification of the residue by silica gel column chromatography (EtOAc/hexanes) furnished the pure product.
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