Phase-transfer-catalyzed asymmetric conjugate cyanation of alkylidenemalonates with KCN in the presence of a Brønsted acid additive

Yan Liu; Seiji Shirakawa; Keiji Maruoka

doi:10.1021/ol400143m

Phase-transfer-catalyzed asymmetric conjugate cyanation of alkylidenemalonates with KCN in the presence of a Brønsted acid additive

Org Lett. 2013 Mar 15;15(6):1230-3. doi: 10.1021/ol400143m. Epub 2013 Mar 5.

Authors

Yan Liu¹, Seiji Shirakawa, Keiji Maruoka

Affiliation

¹ Laboratory of Synthetic Organic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.

PMID: 23461761
DOI: 10.1021/ol400143m

Abstract

Highly enantioselective conjugate cyanation of alkylidenemalonates with KCN was achieved under mild phase-transfer conditions with a bifunctional phase-transfer catalyst. The effect of Brønsted acid additives was examined based on the hypothetical catalytic cycle, and the Brønsted acid additive was found to be essential to promote the conjugate cyanation efficiently.

Publication types

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

MeSH terms

Bromides / chemistry
Catalysis
Malonates / chemistry*
Molecular Structure
Nitriles / chemical synthesis*
Nitriles / chemistry
Potassium Cyanide / chemistry*
Quaternary Ammonium Compounds / chemistry
Stereoisomerism

Substances

Bromides
Malonates
Nitriles
Quaternary Ammonium Compounds
Potassium Cyanide
ammonium bromide