通过催化一锅 Mukaiyama-Aldol 反应立体选择性合成高官能化的α-重氮-β-酮烷酸酯。
Stereoselective synthesis of highly functionalized alpha-diazo-beta-ketoalkanoates via catalytic one-pot Mukaiyama-Aldol reactions.
机构信息
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
出版信息
Org Lett. 2010 Feb 19;12(4):796-9. doi: 10.1021/ol902872y.
Abstract
Methyl diazoacetoacetate undergoes zinc triflate catalyzed condensation with a broad selection of aldehydes to produce delta-siloxy-alpha-diazo-beta-ketoalkanoates in good yield, and delta-hydroxy-alpha-diazo-beta-ketoalkanoates are formed with high diastereoselectivity in reactions with alpha-diazo-beta-ketopentanoate promoted by dibutylboron triflate.
摘要
甲基重氮乙酰乙酸酯在三氟甲磺酸锌催化下与多种醛缩合，高产率地得到δ-硅氧基-α-重氮-β-酮烷酸酯，而在三氟甲磺酸硼二丁酯促进的α-重氮-β-戊酮酸酯反应中，高非对映选择性地得到δ-羟基-α-重氮-β-酮烷酸酯。
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