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Enantioselective Gold-Catalyzed Synthesis of Heterocyclic Compounds

  • Dillon H. Miles
  • F. Dean TosteEmail author
Chapter
Part of the Topics in Heterocyclic Chemistry book series (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.

Keywords

Alkenes Alkynes Allenes Asymmetric catalysis Gold Hydroalkoxylation Hydroamination Hydroarylation Oxazolines Pyrrolidines Tetrahydrofurans 

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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Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of CaliforniaBerkeleyUSA

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