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. 2010 Jan 1;12(1):172-5.
doi: 10.1021/ol9025793.

Catalytic enantioselective formation of chiral-bridged dienes which are themselves ligands for enantioselective catalysis

M Kevin Brown  1 , E J Corey
Affiliations

Catalytic enantioselective formation of chiral-bridged dienes which are themselves ligands for enantioselective catalysis

M Kevin Brown et al. Org Lett. .

Abstract

This paper reports a method for highly enantioselective Diels-Alder reaction with an acetylene equivalent to produce chiral-bridged dienes. These dienes, by coordination to Rh(I), can serve as catalysts for the enantioselective addition of vinyl or aryl groups to alpha,beta-unsaturated ketones.

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Figures

Scheme 1
Scheme 1
Preparation of Norbornadiene-Based Ligands
Figure 1
Figure 1
Investigations into Order of Addition
Scheme 2
Scheme 2
Arylation of Diene 6
Scheme 3
Scheme 3
Preparation of Bicyclooctadiene-Based Ligands
Scheme 4
Scheme 4
Enantioselective Synthesis of 9-Isocyanopupukeanane Intermediate 20
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