Asymmetric Tandem Reactions Achieved by Chiral Amine & Gold(I) Cooperative Catalysis

doi:10.6023/cjoc202209016

Abstract

Cooperative catalysis is a powerful strategy to improve the efficiency and selectivity of organic reactions. It is of current interest in asymmetric catalysis to combine different catalysts to secure synergistic effects to realize high reaction activity and selectivity unattainable by a single catalyst, and to develop challenging new reactions. Depending on their structures, chiral amines can activate aldehydes or ketones with α-protons, conjugated enals or enones, activated methine or methylene compounds via enamine catalysis, iminium catalysis or deprotonative activation. On the other hand, cationic gold(I) catalysis can efficiently activate olefins, alkynes or diazo compounds for functionalization reactions. Therefore, it has attracted ever-increasing attention to combine the reactivity patterns of the two types of catalysts to develop asymmetric tandem reactions, and paves a facile way to construct complex chiral compounds from simple starting materials. The purpose of this review is to introduce the asymmetric tandem reactions achieved by chiral amine & gold(I) catalysis, focusing on the advantages of such type of cooperative catalysis, the way to avoid catalyst deactivation, as well as its future development, so as to provide some useful references for researchers engaged in asymmetric catalysis.

Key words: asymmetric catalysis, cooperative catalysis, chiral amine catalysis, gold catalysis

Cite this article

Xiaoyuan Cui, Feng Zhou, Haihong Wu, Jian Zhou. Asymmetric Tandem Reactions Achieved by Chiral Amine & Gold(I) Cooperative Catalysis[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3033-3050.

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Fig. & Tab. 22

Scheme 1. Multiple catalysts realized cooperative catalysis

Scheme 2. Cooperative amine & Au catalysis

Scheme 3. Enantioselective Michael addition/5-exo-dig cyclization to bicyclic enones

Scheme 4. Enantioselective Diels-Alder/5-exo-dig cyclization reaction to [6,5,6]-carbocyclic enones

Scheme 5. Enantioselective Diels-Alder/7-endo-dig cyclization reaction to annulated pyrroles.

Scheme 6. Enantioselective Michael addition/5-exo-dig cyclization to tetrahydrofuranyl

Scheme 7. Enantioselective Michael addition/6-endo-dig cyclization to bicyclic O,O-acetals.

Scheme 8. Enantioselective α-allylic alkylation reaction to cyclic aldehyde

Scheme 9. Enantioselective intermolecular α-allylic alkylation of α-branched aldehyde

Scheme 10. Enantioselective Michael addition/5-exo-dig cyclization reaction to cyclopentene carbaldehydes

Scheme 11. Enantioselective Michael addition/5-endo-dig cyclization reaction to butenolides

Scheme 12. Enantioselective Diels-Alder/5-endo-dig cyclization reaction to tetrahydrofuro[3-b]pyridines

Scheme 13. Enantioselective Mannich/hydroamination to dihydropyrrole

Scheme 14. Enantioselective Mannich/hydroamination reaction to spirocyclic oxindoles.

Scheme 15. Enantioselective Mannich/hydroamination reaction to tetrahydropyridines or tetrahydropyrrole

Scheme 16. Enantioselective Mannich/hydroamination reaction to bispirocyclic oxindoles

Scheme 17. Enantioselective nucleophilic addition/hydroamination reaction to trispirocyclic oxindoles

Scheme 18. C—H insertion/Michael addition to chiral oxindole

Scheme 19. Enone-formation/cyanosilylation to chiral oxindoles

Scheme 20. Alkenylation/Michael/Michael to chiral spirocyclic oxindoles

Scheme 21. Formal allylation/Michael to chiral benzothiophen-2-ones

Scheme 22. Enantioselective hetero-ene reaction to chiral oxindoles

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手性胺/金(I)协同催化的不对称串联反应研究