Diastereoselective Construction of syn-1,3-Dioxanes via a Bismuth-Mediated Two-Component Hemiacetal/Oxa-Conjugate Addition Reaction
Diastereoselective Construction of syn-1,3-Dioxanes via a Bismuth-Mediated Two-Component Hemiacetal/Oxa-Conjugate Addition Reaction
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DOI：
10.1021/ja208668u
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发表时间：
2012-02-15
影响因子：
15
通讯作者：
Lawler, Michael J.
中科院分区：
文献类型：
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作者：
Evans, P. Andrew;Grisin, Aleksandr;Lawler, Michael J.
铋介导的δ-三烷基甲硅烷氧基和δ-羟基α，β-不饱和醛和酮与烷基醛的双组分半缩醛/氧杂-共轭加成以高效和立体选择性的方式提供了顺式-1，3-二氧杂环己烷。该协议的主要优点是其操作简单，并能够直接访问吸电子基团，而无需求助于氧化态调整。
The bismuth-mediated two-component hemiacetal/oxa-conjugate addition of delta-trialkylsilyloxy and delta-hydroxy alpha,beta-unsaturated aldehydes and ketones with alkyl aldehydes provides the syn-1,3-dioxanes in a highly efficient and stereoselective manner. The key advantages of this protocol are its operational simplicity and its ability to directly access electron-withdrawing groups without recourse to oxidation state adjustments.