Me2(CH2Cl)SiCN: Bifunctional Cyanating Reagent for the Synthesis of Tertiary Alcohols with a Chloromethyl Ketone Moiety via Ketone Cyanosilylation

Xing-Ping Zeng; Jian Zhou

doi:10.1021/jacs.6b05601

Me2(CH2Cl)SiCN: Bifunctional Cyanating Reagent for the Synthesis of Tertiary Alcohols with a Chloromethyl Ketone Moiety via Ketone Cyanosilylation

J Am Chem Soc. 2016 Jul 20;138(28):8730-3. doi: 10.1021/jacs.6b05601. Epub 2016 Jul 11.

Authors

Xing-Ping Zeng¹, Jian Zhou^{1

2}

Affiliations

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 3663N Zhongshan Road, Shanghai 200062, China.
² State Key Laboratory of Elemento-organic Chemistry, Nankai University , Tianjin 300071, P. R. China.

PMID: 27399262
DOI: 10.1021/jacs.6b05601

Abstract

We report a novel bifunctional cyanating reagent, Me2(CH2Cl)SiCN, which paves the way to a one-pot sequential synthesis of tertiary alcohols featuring a chloromethyl ketone moiety via enantioselective ketone cyanosilylation. This method contributes to gram-scale enantioselective total synthesis of the aggregation pheromone of the Colorado potato beetle, (S)-CPB.

Publication types

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