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An Organocatalytic [3+2] Cyclisation Strategy for the Highly Enantioselective Synthesis of Spirooxindoles
Author(s) -
Voituriez Arnaud,
Pinto Nathalie,
Neel Mathilde,
Retailleau Pascal,
Marinetti Angela
Publication year - 2010
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.201001791
Subject(s) - enantioselective synthesis , cyclopentanes , annulation , phosphine , organocatalysis , computer science , chemistry , scheme (mathematics) , combinatorial chemistry , catalysis , organic chemistry , mathematics , mathematical analysis
Power of P : Phosphine‐promoted [3+2] annulation reactions between electron‐poor allenes and 3‐arylidene indolin‐2‐ones afford a new organocatalytic strategy for the synthesis of the spirocyclic core of oxindolic cyclopentanes (see scheme). Asymmetric variants of these reactions have been implemented by using chiral catalysts, giving very high levels of asymmetric induction.