Diastereoselective Aza‐Baylis–Hillman Reactions: Synthesis of Chiral α‐Allenylamines and 2‐Azetines from Allenic Esters | Zendy

Santos Bruna S. | Zendy; Cardoso Ana L. | Zendy; Matos Beja Ana | Zendy; Ramos Silva Manuela | Zendy; Paixão José A. | Zendy; Palacios Francisco | Zendy; Pinho e Melo Teresa M. V. D. | Zendy

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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.

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