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Synfacts 2013; 9(1): 0066
DOI: 10.1055/s-0032-1317775
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Copper-Catalyzed Borylative Aldol Cyclizations

Contributor(s):
Hisashi Yamamoto
,
Kimberly Griffin
Burns AR, González JS, Lam HW * University of Edinburgh, UK
Enantioselective Copper(I)-Catalyzed Borylative Aldol Cyclizations of Enone Diones.

Angew. Chem. Int. Ed. 2012;
51: 10827-10831
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

conjugate boration - aldol cyclization - copper - domino reaction

Significance

The formation of metal enolates allows for precise enolization, as well as potential enantio- and diastereoselective enolization. In this report, the authors apply this idea to a copper-catalyzed conjugate boration–aldol cyclization sequence to produce enantioenriched decalin-, hydrindane- and diquinone-based products.


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Comment

The copper–bisphosphine catalyst system developed, produces decalins as well as [5,6]-, [6,5]-, and [5,5]-bicyclic ring products with high levels of diastereo- and enantioselectivity. Kinetic resolution of a racemic chiral enone also afforded the cyclization product with good diastereo- and enantioselectivity.


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