Diastereodivergent organocatalytic asymmetric vinylogous Michael reactions

Xin Li, Min Lu, Yun Dong, Wenbin Wu, Qingqing Qian, Jinxing Ye () and Darren J Dixon ()
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Xin Li: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology
Min Lu: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology
Yun Dong: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology
Wenbin Wu: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology
Qingqing Qian: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology
Jinxing Ye: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology
Darren J Dixon: Chemistry Research Laboratory, University of Oxford

Nature Communications, 2014, vol. 5, issue 1, 1-9

Abstract: Abstract One of the major challenges of modern asymmetric catalysis is the ability to selectively control the formation of all diastereoisomers of reaction products possessing multiple stereocenters. Pioneers of such diastereodivergent catalytic asymmetric processes have focused on reactions where the newly formed stereogenic centres are proximal to the active carbonyl group. To date, however, diastereodivergent reactions at remote positions remain an unmet challenge. Herein, we describe a catalyst-controlled diastereodivergence in the formation of remote stereocenters in the direct vinylogous Michael reactions of β, γ-unsaturated butenolides to α, β-unsaturated ketones. The reactions are enabled by two complementary, non-enantiomeric multifunctional catalysts, which mutually activate and organise both reactants, affording either the syn- or anti-adduct with high diastereo- and enantioselectivity. These two catalytic systems are also applicable in the Mukaiyama–Michael reactions and tandem Michael–Michael reactions.

Date: 2014
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DOI: 10.1038/ncomms5479

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