Stereoselective Synthesis of β-Amino Ynones by the Addition of Alkynones to Nonracemic Sulfinimines: Formal Total Synthesis of l- Xylo and l- Arabino Phytosphingosines

Polimera Obula Reddy; Arava Amaranadha Reddy; Kavirayani R Prasad

doi:10.1021/acs.joc.9b02938

Stereoselective Synthesis of β-Amino Ynones by the Addition of Alkynones to Nonracemic Sulfinimines: Formal Total Synthesis of l- Xylo and l- Arabino Phytosphingosines

J Org Chem. 2020 Feb 21;85(4):2743-2751. doi: 10.1021/acs.joc.9b02938. Epub 2020 Jan 16.

Authors

Polimera Obula Reddy¹, Arava Amaranadha Reddy¹, Kavirayani R Prasad¹

Affiliation

¹ Department of Organic Chemistry , Indian Institute of Science , Bangalore 560012 , India.

PMID: 31913627
DOI: 10.1021/acs.joc.9b02938

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't