通过双(三氟甲烷磺酰基)酰亚胺介导的二组分半缩醛/氧杂共轭加成反应构建顺式-1,3-二恶烷的立体选择性。
Diastereoselective construction of syn-1,3-dioxanes via a bismuth-mediated two-component hemiacetal/oxa-conjugate addition reaction.
机构信息
Department of Chemistry, The University of Liverpool, Crown Street, Liverpool L69 7ZD, United Kingdom.
出版信息
J Am Chem Soc. 2012 Feb 15;134(6):2856-9. doi: 10.1021/ja208668u. Epub 2012 Feb 1.
PMID:22296255
Abstract
The bismuth-mediated two-component hemiacetal/oxa-conjugate addition of δ-trialkylsilyloxy and δ-hydroxy α,β-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.
摘要
双三甲基硅基缩醛/氧杂共轭加成反应是由双三甲基硅基缩醛和 δ-羟基 α,β-不饱和醛和酮与烷基醛反应，提供了一种高效和立体选择性的方式来合成顺式-1,3-二氧六环。该方法的关键优势在于其操作简单，并且能够直接接入吸电子基团，而无需进行氧化态调节。
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