Diethyl oxomalonate as a three carbon synthon for synthesis of functionalized 1,1′-disubstituted tetrahydroisoquinoline

Bois-Choussy, M.; Cadet, S.; De Paolis, M.; Zhu, J.

doi:10.1016/S0040-4039(01)00776-6

Diethyl oxomalonate as a three carbon synthon for synthesis of functionalized 1,1′-disubstituted tetrahydroisoquinoline

Bois-Choussy, M. ; Cadet, S. ; De Paolis, M. ; Zhu, J.

Pictet–Spengler condensation of β-arylethylamine with diethyl oxomalonate provides an entry to highly functionalized 1,1′-disubstituted tetrahydroisoquinoline in high yield. Selective functionalization of two ester groups is demonstrated. Syntheses and functional group transformations of 1,1-disubstituted tetrahydroisoquinoline are reported.

Published in:

Tetrahedron Letters, 42, 27, 4503-4506

Year:

2001

Publisher:

Elsevier

ISSN:

00404039

Keywords:

1,1′-disubstituted tetrahydroisoquinoline ; Pictet–Spengler reaction ; diethyl oxomalonate ; quaternary carbon ; conformationally constrained amino acid

DOI:

10.1016/S0040-4039(01)00776-6