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Diastereoselective α-Hydroxylation of N-tert-Butanesulfinyl Imidates and N′-tert-Butanesulfinyl Amidines with Molecular Oxygen

Peng-Ju Ma, Hui Liu, Yan-Jun Xu, Haji Akber Aisa and Chong-Dao Lu*

*Key Laboratory of Plant Resources and Chemistry of Arid Zones, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences, Urumqi 830011, China, Email: clums.xjb.ac.cn

P.-J. Ma, H. Liu, Y.-J. Xu, H. A. Aisa, C.-D. Lu, Org. Lett., 2018, 20, 1236-1239.

DOI: 10.1021/acs.orglett.8b00178 (free Supporting Information)


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Abstract

The use of chiral α-alkyl N-tert-butanesulfinyl imidates and α-aryl N′-tert-butanesulfinyl amidines enables a diastereoselective α-hydroxylation using molecular oxygen. The aza-enolates generated from deprotonation of the imidates/amidines react with O2 followed by transformation into α-hydroxylation products in the presence of trimethyl phosphite as reductant.

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rationalization of stereochemistry



Key Words

α-hydroxylation, oxygen, trimethylphosphite


ID: J54-Y2018