Journal
SYNLETT
Volume -, Issue 5, Pages 760-764Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0031-1290532
Keywords
cross-coupling; regioselectivity; alkaloids; alkynes; amines
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Funding
- CSIR, New Delhi, India [01(2138)/07/EMR-II]
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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.
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