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 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 o...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-02, Vol.85 (4), p.2743-2751
Main Authors: Reddy, Polimera Obula, Reddy, Arava Amaranadha, Prasad, Kavirayani R
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02938