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Stereoselective Synthesis of β-Amino Ynones by the Addition of Alkynones to Nonracemic Sulfinimines: Formal Total Synthesis of l-Xylo and l-Arabino Phytosphingosines.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-01-16 , DOI: 10.1021/acs.joc.9b02938
Polimera Obula Reddy 1 , Arava Amaranadha Reddy 1 , Kavirayani R Prasad 1
Affiliation  

The addition of silyl enol ethers obtained from ynones to sulfinimines furnished the corresponding β-sulfinamido ynones in a very good yield and diastereoselectivity. The formed ynones serve as precursors amenable for the synthesis of bioactive compounds. This has been illustrated in the synthesis of l-xylo and l-arabino phytosphingosines.

中文翻译:

通过将炔烃加到非外消旋亚磺胺上的立体选择性合成β-氨基壬烯:l-木糖和l-阿拉伯植物鞘氨醇的正式全合成。

将由炔酮得到的甲硅烷基烯醇醚加到亚磺胺中,以非常好的收率和非对映选择性提供了相应的β-亚磺酰胺基炔酮。形成的炔酮用作适于合成生物活性化合物的前体。在1-xylo和1-阿拉伯糖基植物鞘氨醇的合成中已经说明了这一点。
更新日期:2020-01-17
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