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Enantioselective Gold-Catalyzed Synthesis of Heterocyclic Compounds

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Au-Catalyzed Synthesis and Functionalization of Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 46))

Abstract

Asymmetric gold-catalyzed syntheses of a diverse range of heterocycles are described herein. This chapter outlines efforts toward the construction of these molecules via intermolecular, intramolecular, and tandem cyclization strategies. Additionally, asymmetric hydrogenation and epoxidation approaches are detailed. These methodologies generally utilize substrates containing soft, unsaturated carbon-carbon bonds, which can easily interact with the carbophilic gold atom(s). Mostly through the use of bis- or monophosphine ligands, modest to excellent yields and enantioselectivities are obtained for a variety of partially and fully saturated heterocycles. Although steric variation of the phosphine catalyst is the most commonly used strategy for enantioinduction, the use of chiral counteranions has proven useful for more challenging transformations. This chapter includes only examples of syntheses where a chiral gold catalyst is used in the direct formation of the heterocycle; examples of pendant functionalization of an existing heterocycle or chirality transfer from enantioenriched substrate to product are not included.

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Abbreviations

BINAP:

(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine)

BINOL:

1,1′-Bi-2-naphthol

C3-TunePhos:

1,13-Bis(diphenylphosphino)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin

Cl-MeO-BIPHEP:

(5,5′-Dichloro-6,6′-dimethoxy-1,1'-biphenyl)-2,2′-diyl-bis(diphenylphosphine)

DCE:

1,2-Dichloroethane

DCM:

Dichloromethane

DIPAMP:

1,2-Bis[(2-methoxyphenyl)(phenylphosphino)]ethane

DM-BINAP:

1,1′-Binaphthalene-2,2′-diyl)bis[bis(3,5-dimethylphenyl)phosphine]

DM-SEGPHOS:

5,5′-Βis[di(3,5-xylyl)phosphino]-4,4′-bi-1,3-benzodioxole

dppm:

1,1-Bis(diphenylphosphino)methane

DTBM-MeO-BIPHEP:

2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl

DTBM-SEGPHOS:

5,5′-Bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4′-bi-1,3-benzodioxole

ee:

Enantiomeric excess

IMes:

1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene

NAC:

Nitrogen acyclic carbene

NHC:

N-Heterocyclic carbene

PNB:

4-Nitrobenzoate

SEGPHOS:

5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

SPINOL:

1,1′-Spirobiindane-7,7′-diol

TADDOL:

α,α,α,α-Tetraaryl-1,3-dioxolane-4,5- dimethanol

TFA:

Trifluoroacetate

THF:

Tetrahydrofuran

TRIP:

3,3′-Bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl phosphate

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Authors and Affiliations

  1. Department of Chemistry, University of California, Berkeley, CA, 94720, USA

    Dillon H. Miles & F. Dean Toste

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  1. Dillon H. Miles
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Correspondence to F. Dean Toste .

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  1. Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Bologna, Italy

    Marco Bandini

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Miles, D.H., Toste, F.D. (2015). Enantioselective Gold-Catalyzed Synthesis of Heterocyclic Compounds. In: Bandini, M. (eds) Au-Catalyzed Synthesis and Functionalization of Heterocycles. Topics in Heterocyclic Chemistry, vol 46. Springer, Cham. https://doi.org/10.1007/7081_2015_5003

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