通过Petasis亚甲基化和酸诱导环化反应由β-氨基酸合成哌啶酮。
Beta-amino acids to piperidinones by Petasis methylenation and acid-induced cyclization.
作者信息
Adriaenssens Louis V, Hartley Richard C
机构信息
WestCHEM Department of Chemistry, University of Glasgow, Glasgow, G12 8QQ, United Kingdom.
出版信息
J Org Chem. 2007 Dec 21;72(26):10287-90. doi: 10.1021/jo7019948. Epub 2007 Nov 14.
PMID:17999535
Abstract
Ester-imine derivatives of beta-amino acids were methylenated with dimethyltitanocene under microwave irradiation and the resulting enol ethers cyclized with Brönsted acid or triisopropylaluminium to give 2,6-syn-disubstituted piperidinones in good yield and diastereoselectivity. The method is analogous to the Petasis-Ferrier rearrangement of 1,3-dioxan-4-ones to give tetrahydropyranones.
摘要
在微波辐射下，β-氨基酸的酯-亚胺衍生物用二甲基钛茂进行亚甲基化反应，所得的烯醇醚与布朗斯特酸或三异丙基铝环化，以良好的产率和非对映选择性得到2,6-顺式二取代哌啶酮。该方法类似于1,3-二氧六环-4-酮的Petasis-Ferrier重排反应生成四氢吡喃酮。
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