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Synfacts 2014; 10(9): 0939
DOI: 10.1055/s-0034-1378638
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Copper-Catalyzed 1,4-Addition and Enolate Trapping

Contributor(s):
Mark Lautens
,
Zafar Qureshi
Calvo BC, Madduri AV. R, Harutyunyan SR, Minnaard AJ * University of Groningen, The Netherlands
Copper-Catalysed Conjugate Addition of Grignard Reagents to 2-Methylcyclopentenone and Sequential Enolate Alkylation.

Adv. Synth. Catal. 2014;
356: 2061-2069
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Further Information

Publication History

Publication Date:
18 August 2014 (online)

 
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Key words

copper - bisphosphine ligands - conjugate addition

Significance

The copper-catalyzed Michael addition is a well-studied area of organic chemistry. Following the initial conjugate addition, the resultant enolate can be protonated or trapped by an electrophile to obtain more complex structures in a single step. The authors report an asymmetric 1,4-addition of alkyl Grignard reagents into methylcyclopentenone to produce a highly substituted cyclopentanone core.


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Comment

Excellent conversions and good to modest enantioselectivites were obtained for the examples presented, except for a branched Grignard reagent, which gave a racemic product. This publication is limited to reactions of 2-methylcyclopentenone and unfunctionalized Grignard reagents. The authors report a substantial scope for the enolate trapping with good diastereoselectivities.


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