Stereoselective Formation of Amines

292 Pages·2014·26.38 MB·English

by  Wei Li

Topics in Current Chemistry 343
Wei Li
Xumu Zhang Editors
Stereoselective
Formation of
Amines
343
Topics in Current Chemistry
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Wei Li Xumu Zhang
l
Editors
Stereoselective Formation
of Amines
With contributions by
(cid:1) (cid:1) (cid:1) (cid:1)
A.B. Charette Q.-H. Fan G.K. Friestad Y.-M. He
(cid:1) (cid:1) (cid:1) (cid:1)
K.C. Hultzsch W. Li V. Lindsay A.J. Nawara-Hultzsch
(cid:1) (cid:1) (cid:1) (cid:1)
A.L. Reznichenko F.-T. Song C. Wang J. Xiao
(cid:1) (cid:1)
J.-H. Xie X. Zhang Q.-L. Zhou
Editors
WeiLi XumuZhang
InstituteofChemicalBiologyand DepartmentofChemistryandChemical
DrugDiscovery Biology,DepartmentofMedicinal
StonyBrookUniversity Chemistry
StonyBrook,NY Rutgers,TheStateUniversityofNewJersey
USA Piscataway,NJ
USA
ISSN0340-1022 ISSN1436-5049(electronic)
ISBN978-3-642-53928-2 ISBN978-3-642-53929-9(eBook)
DOI10.1007/978-3-642-53929-9
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Preface
Chiral amines are widespread structural units in chiral auxiliaries and bioactive
molecules, such as agrochemicals and active pharmaceutical ingredients. Histori-
cally, there has been interest in producing chiral amines, and such interest has
promoted a variety of methodologies to synthesize chiral amines – ideally in a
singleisomer.Organicchemists,particularlyorganometallicchemistryresearchers,
have made tremendous strides toward developing novel chemical technologies to
tackle the long-standing challenge of producing chiral amines via operationally
simple,economic,andhighlystereoselectivemethods.
Despite the fact that chiral amines have been recognized for their importance
datingbackseveraldecades,thetoplong-existingchallengesonthelisthavebeen
narrowsubstratescope,relativelylowturnovernumberscausedbycatalystinhibi-
tion/deactivation by amine products, and the necessity of protecting groups. Fol-
lowingtheseminalstudiesinthe1990s,inmorerecentyearsafast-growingbodyof
creativeresearchhasemerged,yieldingversatileandpowerfultransformationsfor
introducing chiral amines stereoselectively. This array of methods has made this
once challenging ambition easier to realize. These new methods have drastically
shortened possible routes to a given natural product or pharmaceutical drug con-
taining a chiral amine moiety. The increasingly versatile development of new
methodswillbeimplementedintonovelsyntheticstrategiesinthefuture.
Thisvolumecontainsvaluableandinsightfulcontributionsfromseveralleading
experts in this field, and the reviews within collectively provide an overview of a
diverse set of valuable approaches as well as their implementation toward natural
product and pharmaceutical synthesis. Asymmetric free radical addition to imino
compounds is addressed in the first chapter, mainly dealing with the use of chiral
hydrazonesasradicalacceptors.Thesecondchapterpresentsanin-depthreviewof
the nucleophilic addition of unstabilized carbanions to azomethine derivatives.
With a biased emphasis on asymmetric hydrogenation methodology, the
subsequentthreechaptersprovide anin-depthoverview ofthe mostpowerfuland
straightforward asymmetric transformations using hydrogen as the reducing re-
agent on three main substrate categories: enamide/enamine, imine, and
v
vi Preface
heteroaromatics,respectively.Acomprehensivecontributiononasymmetrichydro-
amination displays solid examples of efficient catalyst systems that underline the
usefulnessofthedirectadditionofN–Hbondsacrossanunsaturatedcarbon–carbon
bondtoformalchiralamines.Thefinalsectioncoverscurrentmethodsandrecent
advances in asymmetric reductive amination by hydrogenation, transfer hydroge-
nation, organocatalytic reduction, and biocatalytic reduction, as a review of the
state-of-the-artmethodofasymmetricreductiveamination.Unfortunately,wewere
unabletoincludeotherimportanttopicslikeenantioselectiveC–Hamination,and
recently-emerging enzymatic approaches via dynamic kinetic resolution or trans-
aminasetechnologyaschaptersinthisshortvolume.
Wewouldliketoexpressoursinceregratitudetothosewhocontributedtothis
volume.Weappreciatetheirvaluabletimeandeffortandexpectthattheirviewson
futureresearchtrendswillbeusefultoallresearchersinthefield.
Rutgers,TheStateUniversityofNewJersey,Piscataway,NJ,USA XumuZhang
StonyBrookUniversity,StonyBrook,NY,USA WeiLi
September2013
Contents
ControlofAsymmetryintheRadicalAdditionApproachtoChiral
AmineSynthesis ................................................................ 1
GregoryK.Friestad
StereoselectiveFormationofAminesbyNucleophilicAddition
toAzomethineDerivatives .................................................... 33
Andre´ B.CharetteandVincentLindsay
TransitionMetal-CatalyzedEnantioselectiveHydrogenation
ofEnamidesandEnamines ................................................... 75
Qi-LinZhouandJian-HuaXie
AsymmetricHydrogenationofImines ...................................... 103
WeiLiandXumuZhang
AdvancesinTransitionMetal-CatalyzedAsymmetricHydrogenation
ofHeteroaromaticCompounds ............................................. 145
Yan-MeiHe,Feng-TaoSong,andQing-HuaFan
AsymmetricHydroamination ............................................... 191
AlexanderL.Reznichenko,AgnieszkaJ.Nawara-Hultzsch,
andKaiC.Hultzsch
AsymmetricReductiveAmination .......................................... 261
ChaoWangandJianliangXiao
Index .......................................................................... 283
vii
TopCurrChem(2014)343:1–32
DOI:10.1007/128_2013_481
#Springer-VerlagBerlinHeidelberg2013
Publishedonline:28September2013
Control of Asymmetry in the Radical
Addition Approach to Chiral Amine
Synthesis
GregoryK.Friestad
Abstract The state-of-the-science in asymmetric free radical additions to imino
compounds is presented, beginning with an overview of methods involving
stereocontrol by various chiral auxiliary approaches. Chiral N-acylhydrazones are
discussedwithrespecttotheiruseasradicalacceptorsforMn-mediatedintermolecular
additions,fromdesigntoscopesurveystoapplicationstobiologicallyactivetargets.
A variety of aldehydes and ketones serve as viable precursors for the chiral
hydrazones,andavarietyofalkyliodidesmaybeemployedasradicalprecursors,as
discussed in a critical review of the functional group compatibility of the reaction.
Applications to amino acid and alkaloid synthesis are presented to illustrate the
syntheticpotentialoftheseversatilestereocontrolledcarbon–carbonbondconstruction
reactions.Asymmetriccatalysisisdiscussed,fromseminalworkonthestereocontrol
of radical addition to imino compounds by non-covalent interactions with stoichio-
metricamountsofcatalysts,tomorerecentexamplesdemonstratingcatalystturnover.
Keywords Asymmetricsynthesis(cid:1)Hydrazones(cid:1)Imines(cid:1)Oximeethers(cid:1)Radical
reactions
Contents
1 BackgroundandIntroduction................................................................ 2
2 IntermolecularRadicalAdditiontoChiralN-Acylhydrazones............................. 3
2.1 UseofChiralAuxiliariesinRadicalAdditionstoIminoCompounds............... 3
2.2 DesignofChiralN-Acylhydrazones................................................... 5
2.3 PreparationandInitialReactivityStudiesofChiralN-Acylhydrazones............. 6
2.4 Manganese-MediatedRadicalAddition:DiscoveryandMethodDevelopment..... 10
2.5 HybridRadical–IonicAnnulation..................................................... 12
2.6 ApplicationsinAminoAcidSynthesis................................................ 16
G.K.Friestad(*)
DepartmentofChemistry,UniversityofIowa,IowaCity,IA52242,USA
e-mail:[email protected]
2 G.K.Friestad
2.7 ConsiderationsforSynthesisDesignUsingMn-MediatedRadicalAddition........ 21
3 AsymmetricCatalysisofRadicalAddition................................................. 24
4 Summary...................................................................................... 28
References........................................................................................ 29
1 Background and Introduction
Chiral α-branched amine functionalities are present in a wide range of bioactive
synthetictargets,bothnaturalandunnatural.Accordingly,avarietyofmethodsfor
asymmetricaminesynthesishavebeendevelopedoverrecentyears,manyofwhich
involve carbon–carbon bond constructions by addition to the C¼N bond of car-
bonyliminoderivatives,representedintheretrosyntheticdirectioninFig.1(Recent
reviews:see[1–10]).
As is typical in most synthetic chemistry, methods accrue higher impact if they
offer configurational control under mild conditions compatible with a range of
spectator functional groups. Unfortunately, many methods involving nucleophilic
additionsofcarbanion-typereagentstoC¼Nbondshavelimitedcompatibilitywith
electrophilicoracidicfunctionality,ormayresultincompetingdeprotonationatthe
imine α-carbon due to the basicity of the organometallic reagent (For examples of
aza-enolizationofiminocompoundsbyorganometallicreagentssee[11–14]).These
limitationshavespurredthedevelopmentoffreeradicaladditions(Reviewsoffree
radical reactions in synthesis: see [15–21]) to imino compounds (Fig. 2) as a C–C
bond construction approach to chiral amines under mild conditions, offering a
valuable complement to organometallic additions and expanding the scope of this
α-C–C retrosynthetic disconnection (Reviews of radical additions to imines and
relatedacceptors:see[2,22–25]).
Seeking to probe the improved versatility which might be associated with the
radical addition approach, we initiated a program to develop a variety of radical
additions to imino compounds [26]. In the process we introduced several new
modesofstereocontrolusinghydrazonesastheC ¼ Nradicalacceptorfunctionality.
Iminocompoundshavebeenextensivelyusedforcyclizations[27],andinitiallywe
built upon this foundation by introducing a temporary tethering approach [28–34]
which has been effective in establishing relative configuration in a predictable
diastereoselective fashion via reactions of α-hydroxyaldehyde hydrazones(Reviews
oftemporarytethers:see[35–43]).Inthisreviewwewillfocusontheintermolecular
variant of the reaction, for which we have introduced methodology to build chiral
amines from achiral precursors using chiral auxiliaries or chiral catalysts for
stereocontrol[44];thedesignandexperimentalevaluationofthesestrategieswillbe
describedalongwithsyntheticapplications.