PALLADIUM-CATALYZED CYCLIZATION OF ENANTIOPURE ALLENIC LACTAMS PREPARED FROM A PYROGLUTAMIC ACID-DERIVED ORGANOZINE REAGENT

Authors
KARSTENS WFJ STOL M RUTJES FPJT HIEMSTRA H
Citation
Wfj. Karstens et al., PALLADIUM-CATALYZED CYCLIZATION OF ENANTIOPURE ALLENIC LACTAMS PREPARED FROM A PYROGLUTAMIC ACID-DERIVED ORGANOZINE REAGENT, Synlett, (10), 1998, pp. 1126
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
10
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):10<1126:PCOEAL>2.0.ZU;2-9
Abstract
A route for the synthesis of enantiopure allene-substituted lactams ha s been developed. The key-step involves the copper(I) mediated S(N)2' substitution of propargylic tosylates by a (S)-pyroglutamic acid deriv ed organozinc reagent. Pd-catalysed reaction of these allenes with iod obenzene afforded enantiopure bicyclic enamides. Furthermore the unexp ected formation of an interesting diene is reported.