Aminocatalytic stereoselective synthesis of (E)-α-naphthyl enals via cross-coupling-like reaction of 1-bromo-2-naphthols with enals

A diphenyl prolinol TMS ether-catalyzed stereoselective reaction of 1-bromo-2-naphthols with enals has been developed. The organocatalyzed cross coupling-like reaction servers an efficient approach to sterically congested (E)-& alpha;-naphthyl enals. The formal C(sp2)-C(sp2) cross-coupling products are obtained in good yields and with excellent stereoselectivities in favor of E-isomers. A broad range of aromatic enals and 1-bromo-2-naphthols are tolerated. The synthetic strategy significantly expands the scope of the organocatalytic cross-coupling-like re-actions by enabling sterically demanding 1-bromo-2-naphthols as viable substrates.

Automated summary

A stereoselective reaction catalyzed by diphenyl prolinol TMS ether has been developed for the synthesis of (E)-α-naphthyl enals, with good yields and excellent stereoselectivities favoring E-isomers. This method allows for a wide range of aromatic enals and 1-bromo-2-naphthols, significantly expanding the scope of organocatalytic cross-coupling-like reactions by enabling sterically demanding substrates.