Search

A two‐step protocol involving cyclization and deprotection towards the synthesis of C‐1 arylated benzazepines has been developed under transition‐metal oxidant free conditions. The coupling reaction of α ‐lithiated carbanion, generated from Boc‐protected amine, with in situ generated aryne proceeds well intramolecularly. A variety of substrates were explored with corresponding products in moderate yield. [ABSTRACT FROM AUTHOR]

Direct cross-coupling between N-methyltetrahydroisoquinolines and alkynes using CuI-DEAD is presented. It affords the regioselective C-1-alkynylated products in good yield. This regioselectivity is in contrast to the results reported earlier in the reaction of N,N-dimethylbenzyl amine where the N-methyl alkynylated product was formed exclusively or predominantly. The C-1-substituted propargylic isoquinolines were easily reduced to phenethylisoquinolines with Pd/C. This reaction sequence provides a short route to synthesize methopholine, homolaudanosine and other phenethylisoquinoline alkaloids. [ABSTRACT FROM AUTHOR]

Abstract: An efficient asymmetric Michael addition of cyclic ketones to β-nitrostyrenes using secondary diamine as an organocatalyst derived from l-proline and (R)-α-methylbenzyl amine has been described. This pyrrolidine based catalyst 1 was found to be very effective to synthesize various γ-nitrocarbonyl compounds in good yield (up to 81%) with excellent stereoselectivity (up to >99:1 dr and >99% ee). [Copyright &y& Elsevier]