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Synfacts 2005(0): 0061-0061
DOI: 10.1055/s-2005-869919
DOI: 10.1055/s-2005-869919
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Pd-Catalyzed Allylic Alkylation of Ketones
Contributor(s): Hisashi Yamamoto, Matthew BoxerB. M. Trost*, J. Xu
Stanford University, USA
Regio- and Enantioselective Pd-Catalyzed Allylic Alkylation of Ketones through Allyl Enol Carbonates
J. Am. Chem. Soc. 2005, 127: 2846-2847
Stanford University, USA
Regio- and Enantioselective Pd-Catalyzed Allylic Alkylation of Ketones through Allyl Enol Carbonates
J. Am. Chem. Soc. 2005, 127: 2846-2847
Further Information
Publication History
Publication Date:
20 July 2005 (online)
Key words
allylic alkylation - allyl enol carbonate - palladium
Significance
The synthesis of α-chiral quaternary cyclohexanones has remained a challenge in organic synthesis. This report shows excellent yields with ee’s over 90% for many substrates and thus is an important step for total syntheses.
Comment
Asymmetric allylation of reactive ketone enolates is a challenging issue of organic synthesis. This paper reports a method to create both tertiary and quaternary stereoecenters α- to ketones, and mark an important advance in this area.
Similar results were reported last year: D. Behenna, B. M. Stoltz J. Am. Chem. Soc. 2004, 126, 15044-15055.