Catalyzed Reactions of Enol Ethers with S_N1 Active Groups: A Novel Method for the Preparation of α‐Alkylated Ketones

Abstract

The performance of tert-alkylations, alkoxyalkylations, and aldehyde enolate allylations proceeding with low catalyst loading (0.1 mol % ± 5 mol %) is described. The reactions are complete within short times and can even be performed without solvent and under ambient conditions. The mechanism of the reaction was investigated by deuterium labeling and cross-over studies.

The Heck-type arylation of allylic alcohols with arenediazonium salts

“…The NMR data of 4aa [15], 4ca [16], 4fa [17], 7ac [18], 7ad [19], 8ad [20], 7fd [21], 8fd [22] were in agreement with literature.…”

Recent Advances in Silver‐Catalyzed Transformations of Electronically Unbiased Alkenes and Alkynes

“…α ‐Alkylated aryl ketones represent one of the most significant class of organic compounds possessing multiple pharmacological and physiological activities. However, challenges still remained for the synthesis of these compounds, such as the employment of stoichiometric amounts of strong bases, limitation to some special substrates and multiple operation steps . Recently, Chung and co‐workers reported a convenient approach to various α ‐alkylated aryl ketones from internal alkynes and benzyl alcohols (Scheme ) .…”

Enantioselective [1,3] O-to-C rearrangement: dearomatization of alkyl 2-allyloxy/benzyloxy-1/3-naphthoates catalyzed by a chiral π–Cu(ii) complex

“…In 2002 and 2003, Gansäuer demonstrated that, in the presence of catalytic amount of Cu(OTf) 2 , the vinyl ether could lead to [1,3] and [3,3] products in 1 : 1 ratio (Scheme 1a). 7 In the year 2005, Rovis reported the regioselective [1,3] rearrangement of allyl vinyl ether catalyzed by aluminum and copper Lewis acids 8. They mentioned that the rearrangement of trisubstituted alkenes would preferentially produce the [1,3] adduct due to steric congestion for normal [3,3] rearrangement.…”