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Phosphine‐Free Palladium‐Catalyzed Allene Carbopalladation/Allylic Alkylation Domino Sequence: A New Route to 4‐(α‐Styryl) γ‐Lactams
Author(s) -
Kammerer Claire,
Prestat Guillaume,
Madec David,
Poli Giovanni
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900184
Subject(s) - palladium , allene , domino , phosphine , tsuji–trost reaction , allylic rearrangement , chemistry , stereochemistry , alkylation , sequence (biology) , medicinal chemistry , catalysis , combinatorial chemistry , organic chemistry , biochemistry
Free to decide : Various 4‐(α‐styryl) γ‐lactams are synthesized in 61–88 % yield by a phosphine‐free palladium‐catalyzed carbopalladation/allylic alkylation domino sequence (see scheme). The cyclization is totally regio‐ and diastereoselective in favor of the 3,4‐ trans ‐disubstituted γ‐lactam. The process is successfully applied to the synthesis of a new aza analogue of the naturally occurring lignan (+)‐oxo‐parabenzlactone.