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Updated: Sep 20, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Highly diastereoselective strecker reaction of enolizable aliphatic sulfinimines
Bin-Feng Li1, Ke Yuan, Ming-Jie Zhang
1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Abstract:
The reaction of chiral sulfinimines 1c-g derived from aliphatic aldehydes with TMSCN in the presence of CsF gave alpha-amino nitriles in high diastereoselectivity and yield. alpha,beta-Diamino acid derivatives were also obtained in high diastereoselectivity from the reaction of 2-aziridinesulfinimines 1h and 1i followed by ring-opening of the products with thiophenol. The presence of hydrogen at the alpha-position of the C=N double bond is crucial in this TMSCN addition reaction.
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