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Asymmetric Hydroamination

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Stereoselective Formation of Amines

Part of the book series: Topics in Current Chemistry ((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.

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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

N t :

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

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Acknowledgment

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

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Authors and Affiliations

  1. Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ, 08854-8087, USA

    Alexander L. Reznichenko, Agnieszka J. Nawara-Hultzsch & Kai C. Hultzsch

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  1. Alexander L. Reznichenko
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  2. Agnieszka J. Nawara-Hultzsch
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  3. Kai C. Hultzsch
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Correspondence to Kai C. Hultzsch .

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Editors and Affiliations

  1. Institute of Chemical Biology and Drug Discovery, Stony Brook University, Stony Brook, New York, USA

    Wei Li

  2. Department of Chemistry & Chemical Biology, Department of Medicinal Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey, USA

    Xumu Zhang

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Reznichenko, A.L., Nawara-Hultzsch, A.J., Hultzsch, K.C. (2013). Asymmetric Hydroamination. In: Li, W., Zhang, X. (eds) Stereoselective Formation of Amines. Topics in Current Chemistry, vol 343. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2013_500

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