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Diastereoselective Aza‐Baylis–Hillman Reactions: Synthesis of Chiral α‐Allenylamines and 2‐Azetines from Allenic Esters
Author(s) -
Santos Bruna S.,
Cardoso Ana L.,
Matos Beja Ana,
Ramos Silva Manuela,
Paixão José A.,
Palacios Francisco,
Pinho e Melo Teresa M. V. D.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901415
Subject(s) - dabco , chemistry , moiety , cycloaddition , reactivity (psychology) , baylis–hillman reaction , stereoselectivity , enantioselective synthesis , stereochemistry , organocatalysis , organic chemistry , catalysis , medicine , alternative medicine , pathology
The reactivity of allenic esters towards activated N ‐sulfonylimines in the presence of DABCO was explored. A formal [2+2] cycloaddition of benzyl buta‐2,3‐dienoate and N ‐arylidenebenzenesulfonamides yielded mainly 2‐methyleneazetidines. Interestingly, a DABCO‐catalysed reaction of 2,3‐allenoates, bearing a chiral auxiliary on the ester moiety, with N ‐arylidenebenzenesulfonamides led to optically active aza‐Baylis–Hillman products and 2‐azetine derivatives.