【摘 要】
：
Fluorinated enol silyl ethers were served as ideal equivalents of α-fluorinated ketones for selective fluoroalkylation under mild condition.We are interest
【机 构】
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Shanghai Key Laboratory of Green Chemistry and Chemical Process,School of Chemistry and Molecular En
【出 处】
：
中国化学会全国第十二届有机合成化学学术研讨会
论文部分内容阅读
Fluorinated enol silyl ethers were served as ideal equivalents of α-fluorinated ketones for selective fluoroalkylation under mild condition.We are interested in the utilization of fluorinated enol silyl ethers for new reaction design,as both mono-and difluorinated enol silyl ethers can be readily accessed from simple materials.1 Previously,we have developed an efficient “on water” catalyst-free aldol reaction of difluoroenoxysilances with aldehydes and activated ketones.2 But this method is not workable for monofluorinated enol silyl ethers.Here,we use the methanol as solvent enables an efficient catalyst-free aldol reaction of tryptanthrin with both mono-and difluorinated enol silyl ethers,giving the desired tertiary alcohols in up to 99%yield and 6:1 dr.If the products operated in a one-pot fashion,the sequential Baeyer-Villiger oxidation and ester-exchanging reaction would readily provide the difluoro analogue of Phaitanthrin B,and it could also be converted to amide or diol.The mild reaction condition,along with the catalyst-free nature,makes our protocol attractive for the synthesis of tryptanthrin based fluorinated compounds for medicinal research.
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