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Review
. 2016 Sep 16:12:2038-2045.
doi: 10.3762/bjoc.12.192. eCollection 2016.

Enantioconvergent catalysis

Justin T Mohr  1 , Jared T Moore  2 , Brian M Stoltz  2
Affiliations
Review

Enantioconvergent catalysis

Justin T Mohr et al. Beilstein J Org Chem. .

Abstract

An enantioconvergent catalytic process has the potential to convert a racemic starting material to a single highly enantioenriched product with a maximum yield of 100%. Three mechanistically distinct approaches to effecting enantioconvergent catalysis are identified, and recent examples of each are highlighted. These processes are compared to related, non-enantioconvergent methods.

Keywords: asymmetric catalysis; enantioselectivity; synthetic methods.

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Figures

Figure 1
Figure 1
Enantioconvergent methods.
Figure 2
Figure 2
Stereomutative enantioconvergent catalysis.
Scheme 1
Scheme 1
Dynamic kinetic resolution by hydrogenation.
Scheme 2
Scheme 2
Enantioconvergent synthesis of phosphines governed by Curtin–Hammett/Winstein–Holness kinetics (TMS = trimethylsilyl, Is = 2,4,6-triisopropylphenyl).
Figure 3
Figure 3
Stereoablative enantioconvergent catalysis.
Scheme 3
Scheme 3
Stoltz’ stereoablative oxindole functionalization.
Scheme 4
Scheme 4
Fu’s type II enantioconvergent Cu-catalyzed photoredox reaction.
Scheme 5
Scheme 5
Stereoablative enantioconvergent allylation and protonation (dba = dibenzylideneacetone).
Scheme 6
Scheme 6
Enantioconvergent allylic alkylation with two racemic starting materials.
Figure 4
Figure 4
Enantioconvergent parallel kinetic resolution.
Scheme 7
Scheme 7
Enantioconvergent parallel kinetic resolution by two complementary biocatalysts.
Scheme 8
Scheme 8
Enantioconvergent PKR by Nocardia EH1.
See this image and copyright information in PMC

References

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