AN EFFICIENT SYNTHESIS OF OXETANONES FROM ALPHA,BETA-EPOXY DIAZOMETHYL KETONES
AN EFFICIENT SYNTHESIS OF OXETANONES FROM ALPHA,BETA-EPOXY DIAZOMETHYL KETONES
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DOI：
10.1016/s0040-4020(01)92288-4
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发表时间：
1992-11-06
期刊：
影响因子：
2.1
通讯作者：
ZWANENBURG, B
中科院分区：
文献类型：
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作者：
THIJS, L;CILLISSEN, PJM;ZWANENBURG, B
α，β-环氧重氮甲基酮1a-h与SnCl4在-78℃的二氯甲烷中反应，得到高产率的β-氯-α-羟基重氮酮3a-h。环氧化环的开环以同步方式进行，构型保持在C(β)。在BF3-OEt2作用下，氯羟基重氮酮3转化为氧乙酮4a-h。对于环氧重氮甲基酮Lb，I-I，不能分离出中间体氯醇3，但以可接受的产率得到了相应的氧乙酮。
Treatment of alpha,beta-epoxy diazomethyl ketones 1a-h with SnCl4 in dichloromethane at -78-degrees-C leads to beta-chloro-alpha-hydroxy diazoketones 3a-h in good yields. The opening of the epoxide ring takes place in a syn manner with retention of configuration at C(beta). The chloro hydroxy diazoketones 3 are converted into the oxetanones 4a-h on treatment with BF3-OEt2. For epoxy diazomethyl ketones lb,i-I the intermediate chlorohydrins 3 could not be isolated, however the corresponding oxetanones were obtained in acceptable yields.