Lewis base catalyzed addition of trimethylsilyl cyanide to aldehydes

Scott E. Denmark, Won Jin Chung

Research output: Contribution to journalArticle

Abstract

A variety of achiral Lewis bases were found to catalyze the addition of TMSCN to the aldehydes. Among them, phosphines and amines were the most efficient catalysts. In addition, several chiral amines and phosphines were examined in a catalytic, asymmetric addition of TMSCN to benzaldehyde albeit with low enantioselectivity. A mechanistic study revealed that the reaction was first order in aldehyde, first order in Lewis base, and zeroth order in TMSCN, suggesting the complex formation of TMSCN and Lewis base formation of complex i. However, there are at least two possible scenarios for this catalytic process, and in view of the low selectivities observed, it is not clear which mechanism is operative.

Original languageEnglish (US)
Pages (from-to)4002-4005
Number of pages4
JournalJournal of Organic Chemistry
Volume71
Issue number10
DOIs
StatePublished - May 12 2006

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Lewis base catalyzed addition of trimethylsilyl cyanide to aldehydes'. Together they form a unique fingerprint.

  • Cite this