Asymmetric Hydroamination

  • Alexander L. Reznichenko
  • Agnieszka J. Nawara-Hultzsch
  • Kai C. Hultzsch
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 343)

Abstract

The direct addition of amine N–H bonds across an unsaturated carbon–carbon linkage gives fast and highly atom-economical access to amines. This review provides an overview of the most effective stereoselective methods using various catalyst systems based on alkali, alkaline earth, and transition metals, as well as enzymatic and organocatalytic approaches. Except for a few sporadic examples in the last century, this field has evolved primarily over the last decade. Catalyst systems have reached enantioselectivities exceeding 90% ee for many substrate classes, but significant challenges remain, in particular in the stereoselective intermolecular hydroamination of unactivated alkenes.

Keywords

Alkenes Amines Asymmetric catalysis Brønsted acid catalysis Heterofunctionalization Hydroamination Nitrogen heterocycles Transition metal catalysis 

Abbreviations

Ar

Aryl

BDPP

2,4-Bis(diphenylphosphino)pentane

BINAP

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl

Bn

Benzyl

Boc

tert-Butoxycarbonyl

Bu

Butyl

cat

Catalyst

Cbz

Benzyloxycarbonyl

COD

Cyclooctadiene

COE

Cyclooctene

Cp*

Pentamethylcyclopentadienyl

Cy

Cyclohexyl

d

Day(s)

DCE

1,2-Dichloroethane

DCM

Dichloromethane

DIOP

Bis(diphenylphosphino-methyl)-2,2-dimethyl-1,3-dioxolane

DMF

Dimethylformamide

dr

Diastereomer ratio

ebthi

Ethylenebis(tetrahydroindenyl)

ee

Enantiomer excess

equiv

Equivalent(s)

Et

Ethyl

Fmoc

Fluorenylmethoxycarbonyl

Grubbs-I

Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium

Grubbs-II

Benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinyl-idene]dichloro(tricyclohexylphosphine)ruthenium

h

Hour(s)

i-Pr

Isopropyl

KHMDS

Potassium hexamethyldisilazide potassium bis(trimethylsilyl)amide

LDA

Lithium diisopropylamide

Mbs

p-Methoxy benzenesulfonyl

Me

Methyl

MeO-BIPHEP

6,6-Dimethoxy-2,2-bis(diphenylphosphino)-1,1-biphenyl

Mes

Mesityl 2,4,6-trimethylphenyl

mol

Mole(s)

MS

Molecular sieves

Mts

Mesitylenesulfonyl

MW

Microwave

Nf

Nonafluorobutanesulfonyl

NMO

N-Methylmorpholine N-oxide

Nt

Turnover frequency

PAL

Phenylalanine ammonia lyase

PG

Protecting group

Ph

Phenyl

PMB

4-Methoxyphenyl

PNB

4-Nitrobenzoyl

rt

Room temperature

SEGPHOS

4,4′-Bi-1,3-benzodioxole-5,5′-diylbis(diphenylphosphane)

TBDPS

tert-Butyldiphenylsilyl

TBS

tert-Butyldimethylsilyl

t-Bu

tert-Butyl

Tf

Trifluoromethanesulfonyl (triflyl)

TFAA

Trifluoroacetic anhydride

THF

Tetrahydrofuran

TiPP

2,4,6-Triisopropyphenyl

TIPS

Triisopropylsilyl

Tol

4-Methylphenyl

Troc

2,2,2-Trichloroethoxycarbonyl

Ts

Tosyl 4-toluenesulfonyl

Xylyl-BINAP

2,2′-Bis[di(3,5-xylyl)phosphino]-1,1′-binaphthyl

Notes

Acknowledgment

Generous financial support by the National Science Foundation through a NSF CAREER Award (CHE 0956021) is gratefully acknowledged.

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Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  • Alexander L. Reznichenko
    • 1
  • Agnieszka J. Nawara-Hultzsch
    • 1
  • Kai C. Hultzsch
    • 1
  1. 1.Department of Chemistry and Chemical BiologyRutgers, The State University of New JerseyPiscatawayUSA

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