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Synthesis of Chiral Spirocyclopentenyl‐β‐lactams through Phosphane‐Catalyzed [3+2] Annulation of Allenoates with 6‐Alkylidenepenicillanates
Author(s) -
Santos Bruna S.,
Pinho e Melo Teresa M. V. D.
Publication year - 2013
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.201300153
Subject(s) - stereocenter , annulation , chemistry , regioselectivity , substituent , stereochemistry , derivative (finance) , organocatalysis , enantioselective synthesis , catalysis , combinatorial chemistry , organic chemistry , financial economics , economics
The first examples of phosphane‐catalyzed [3+2] annulation of allenoates to 6‐alkylidenepenicillanates leading to chiral spirocyclopentenyl‐β‐lactams are reported. The synthesis of this new type of β‐lactams involved the generation of either two or three consecutive stereogenic centers, including a quaternary chiral center. Although the reported methodology is highly diastereoselective, the regioselectivity is dependent on the nature of the methylenepenicillanate derivative and on the nature of the allenoate γ‐substituent.