Pictet-Spengler condensation of N-sulfonyl-beta-phenethylamines with alpha-chloro-alpha-phenylselenoesters. New synthesis of 1,2,3,4-tetrahydroisoquinoline-1-carboxylates

Authors
Silveira, CC Bernardi, CR Braga, AL Kaufman, TS
Citation
Cc. Silveira et al., Pictet-Spengler condensation of N-sulfonyl-beta-phenethylamines with alpha-chloro-alpha-phenylselenoesters. New synthesis of 1,2,3,4-tetrahydroisoquinoline-1-carboxylates, TETRAHEDR L, 40(27), 1999, pp. 4969-4972
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
27
Year of publication
1999
Pages
4969 - 4972
Database
ISI
SICI code
0040-4039(19990702)40:27<4969:PCONWA>2.0.ZU;2-9
Abstract
The reaction of N-sulfonyl-beta-phenethylamines with alpha-chloro-alpha-phe nylseleno acetate/propionate esters under Lewis add promotion gives moderat e to good yields of the corresponding 1, 2,3,4-tetrahydroisoquinoline-1-car boxylates. Varying degrees of diastereoselection were obtained using chiral sulfonamides and/or esters. Employing this strategy. the achievement of a new total synthesis of Colycotomine is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.