An Organocatalytic Asymmetric Nazarov Cyclization
- 27 May 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (24), 8266-8267
- https://doi.org/10.1021/ja103028r
Abstract
An organocatalytic asymmetric Nazarov cyclization of diketoesters that proceeds by means of a dual activation mechanism has been developed. Screening of a number of catalysts led to a new thiourea that incorporates a primary amino group. The method gives rise to cyclic products with two adjacent quaternary asymmetric carbon atoms, one of which is an all-carbon stereocenter, with complete or nearly complete diastereoselectivity and in high or very high enantiomeric excess. A brief and very convenient synthesis of the acyclic diketoester starting materials through nucleophilic addition to a ketene is also described.Keywords
This publication has 37 references indexed in Scilit:
- Iron- or Cobalt-Catalyzed Nazarov Cyclization: Asymmetric Reaction and Tandem Cyclization-Fluorination ReactionSynlett, 2010
- Tandem Nazarov cyclization–halovinylation of divinyl ketones under Vilsmeier conditions: synthesis of highly substituted cyclopentadienesChemical Communications, 2010
- Enamine-Iminium Ion Nazarov Cyclization of α-KetoenonesOrganic Letters, 2009
- Scaleable catalytic asymmetric Strecker syntheses of unnatural α-amino acidsNature, 2009
- Formal Synthesis of (±)-RoseophilinOrganic Letters, 2008
- Traceless Chiral Auxiliaries for the Allene Ether Nazarov CyclizationThe Journal of Organic Chemistry, 2008
- Construction of aryl-substituted triquinanes through the interrupted Nazarov reactionChemical Communications, 2008
- A Chiral Primary Amine Thiourea Catalyst for the Highly Enantioselective Direct Conjugate Addition of α,α‐Disubstituted Aldehydes to NitroalkenesAngewandte Chemie-International Edition, 2006
- Enantioselective Nazarov Reactions through Catalytic Asymmetric Proton TransferJournal of the American Chemical Society, 2004
- Cyclopentannelation Reaction for Rapid Assembly of Multifunctional Products. (d,l)-Desepoxymethylenomycin a Methyl EsterSynthetic Communications, 1994