A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates

• Erwan Le Gall,
• Antoine Pignon and
• Thierry Martens

Beilstein J. Org. Chem. 2011, 7, 997–1002, doi:10.3762/bjoc.7.112

• -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates is described. This route involves the formation of an imine, which is used without isolation, followed by its activation by the carbonyl-containing electrophile and the trapping of the acyliminium by an organozinc reagent. Most

• steps are conducted concomitantly to render the procedure as practical and straightforward as possible. Therefore, the whole experimental protocol takes less than two hours. Keywords: acyliminium; amides; carbamates; multicomponent reactions; organozinc reagents; Introduction Diarylmethylamines

• group has been involved in various projects pertaining to the development of multicomponent reactions (MCRs) involving organometallic reagents, in particular organozinc reagents, due to their ability to react in very mild conditions and generally preserve most common functional groups. Moreover, used in

Continuous flow enantioselective arylation of aldehydes with ArZnEt using triarylboroxins as the ultimate source of aryl groups

• Julien Rolland,
• Xacobe C. Cambeiro,
• Carles Rodríguez-Escrich and
• Miquel A. Pericàs

Beilstein J. Org. Chem. 2009, 5, No. 56, doi:10.3762/bjoc.5.56

• ]. On the other hand, enantioselective arylation of aldehydes with organozinc reagents appears as a most convenient alternative, since the initial aldehyde undergoing addition presents two very different groups (namely, a H atom and an aryl group) and hence offers good opportunities for enantiocontrol