Regioselective Nucleophilic Addition of Organometallic
Reagents to 3‑Geminal Bis(silyl) N‑Acyl
Pyridinium

Song, Zhenlei

Regioselective Nucleophilic Addition of Organometallic Reagents to 3‑Geminal Bis(silyl) N‑Acyl Pyridinium

Posted on 2014-04-04 - 00:00

A regioselective nucleophilic addition to 3-geminal bis(silyl) N-acyl pyridinium has been described. Geminal bis(silane) shows contrasting roles that lead to different regioselectivities for the addition of different nucleophiles: its steric effect dominates to favor 1,6-addition of alkyl, vinyl, and aryl organometallic reagents; its directing effect dominates to favor 1,2-addition of less sterically demanding alkynyl Grignard reagents.

CITE THIS COLLECTION

Wu, Ya; Li, Linjie; Li, Hongze; Gao, Lu; Xie, Hengmu; Zhang, Zhigao; et al. (2016). Regioselective Nucleophilic Addition of Organometallic Reagents to 3‑Geminal Bis(silyl) N‑Acyl Pyridinium. ACS Publications. Collection. https://doi.org/10.1021/ol500302r

https://doi.org/10.1021/ol500302r

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