Asymmetric Organocatalysis: New Strategies, Catalysts, and Opportunities, 2 Volumes

736 Pages·2022·42.676 MB·English

by  Lukasz Albrecht, Anna Albrecht, Luca Dell'Amico

D
ow
nloaded from
https://onlinelibrary.w
iley.com
/doi/ by ibrahim
ragab - C
ochrane G
erm
any , W
iley O
nline L
ibrary on [23/11/2022]. See the T
erm
s and C
onditions (https://onlinelibrary.w
iley.com
/term
s-and-conditions) on W
iley O
nline L
ibrary for rules of use; O
A
articles are governed by the applicable C
reative C
om
m
ons L
icense
D
ow
nloaded from
https://onlinelibrary.w
iley.com
/doi/ by ibrahim
ragab - C
AsymmetricOrganocatalysis ochrane Germ
any , W
iley O
nline L
ibrary on [23/11/2022]. See the T
erm
s and C
onditions (https://onlinelibrary.w
iley.com
/term
s-and-conditions) on W
iley O
nline L
ibrary for rules of use; O
A
articles are governed by the applicable C
reative C
om
m
ons L
icense
D
ow
nloaded from
https://onlinelibrary.w
iley.com
/doi/ by ibrahim
ragab - C
Asymmetric Organocatalysis ochrane G
erm
any , W
New Strategies, Catalysts, and Opportunities iley Online L
VEodliutemdeb1y Łukasz Albrecht, Anna Albrecht, and Luca Dell’Amico ibrary on [23/11/2022]. See the T
erm
s and C
onditions (https://onlinelibrary.w
iley.com
/term
s-and-conditions) on W
iley O
nline L
ibrary for rules of use; O
A
articles are governed by the applicable C
reative C
om
m
ons L
icense
D
ow
nloaded from
https://onlinelibrary.w
iley.com
/doi/ by ibrahim
ragab - C
Asymmetric Organocatalysis ochrane G
erm
any , W
New Strategies, Catalysts, and Opportunities iley Online L
VEodliutemdeb2y Łukasz Albrecht, Anna Albrecht, and Luca Dell’Amico ibrary on [23/11/2022]. See the T
erm
s and C
onditions (https://onlinelibrary.w
iley.com
/term
s-and-conditions) on W
iley O
nline L
ibrary for rules of use; O
A
articles are governed by the applicable C
reative C
om
m
ons L
icense
D
ow
nloaded from
https://onlinelibrary.w
iley.com
/doi/ by ibrahim
ragab - C
ochrane G
erm
Editors AllbookspublishedbyWILEY-VCHarecarefully any , W
produced.Nevertheless,authors,editors,and iley O
PLIZ9PṖn0rrooeoos-lrdff9tao..zi2ntmŁAu4UdunstkLnnekaaoiiosvedzAfegzlAOrobslrrib1etgr1yceah6cnothfitcTCechhenmoilsotgryy pctipiLnnooirubaonbmbrdctaelaeviirsnfideyrhndrueoeetereftrdahnCodliatofnodltnyeestngrthbtrroaaeoeeittslsreiswessnm.oaCabRrercaornecrooadauttknsdhrNs,taee,dottrrieh.asn:i.tetaacaerlpi,muenpidlfaslloiiudenmrsvdmgtiarsftayaoehttdriiiosotnnobsok,oeke,p nline Library on [23/11/2022]. See the T
LodzUniversityofTechnology erm
ICZ9PPU̇n0roehnos-lref9tiao.vim2ntmLeu4duristsscLektairotioyyeDdfgeozGolfl’eAP1nm1ae6dircoaovlaandEcological BAfBtTtrhhirhobeiictsemlaiDispoDtheatguheulrLboutaeilsgbpticBuscrhhcaareiehircttyrieiNoiesnCncNahfaotoaitiLrrnoatdmiinlbootfaahrngoltaebuariroiliDytbnbnh.lgieiipbo-usuilttnibbhso-olcetPiohhksuhkeebeklidiscliaabstvytisaoinlaDbaleta s and Conditions (https://onlinelibrary.w
DVieapMaratmrzeonloto1fChemicalSciences Ndaattaioanrealabvibaliiloabgrleafioen;tdheetaIinletedrnbiebtlaiotgraphic iley.com
53131Padova <http://dnb.d-nb.de>. /term
ICtoavleyrImage:©alice-photo/Shutterstock ©6A9l4l260ri92g3hWWtseiIrnLehsEeeYrimv-Ve,dCGH(einrGmclmuandbiyHn,gBthosocshesotrfaße12, s-and-conditions) on W
translationintootherlanguages).Nopartof iley O
thisbookmaybereproducedinanyform–by nline L
pmmftrrhoaeaodmactehnomtisphnr–aeeirnnpklatousin,rnbgegtlurti,scaamh.nguesiercsmsrew.oidtiRfittiehelnmdgotiuo,hsttorieswrtrrbearaodinntoytnsekloana,tmtehpeveedeesrrni,mnwtioshsaieonn ibrary for rules of use; O
ncPeeoTyoPPBroipnuDotnebsotFssipkIdIeISSeSteIBBStcBriiNBNenNfidN:g::c99:9au7797lnl8S878yp-t-8-3r3r3m-ao--3-55i5ta-v2e252rec77k27,t--7e-e3C88d-d5383h1a232be2s221yn5029snl--u1-a10a4-cwi7h,.I,nadreianottobe A articles are governed by the applicable C
reative C
om
m
ons L
icense
D
ow
nloaded from
https://onlinelibrary.w
iley.com
/doi/ by ibrahim
ragab - C
ochrane G
erm
Editors AllbookspublishedbyWILEY-VCHarecarefully any , W
produced.Nevertheless,authors,editors,and iley O
PLIZ9PṖn0rrooeoos-lrdff9tao..zi2ntmŁAu4UdunstkLnnekaaoiiosvedzAfegzlAOrobslrrib1etgr1yceah6cnothfitcTCechhenmoilsotgryy pctipiLnnooirubaonbmbrdctaelaeviirsnfideyrhndrueoeetereftrdahnCodliatofnodltnyeestngrthbtrroaaeoeeittslsreiswessnm.oaCabRrercaornecrooadauttknsdhrNs,taee,dottrrieh.asn:i.tetaacaerlpi,muenpidlfaslloiiudenmrsvdmgtiarsftayaoehttdriiiosotnnobsok,oeke,p nline Library on [23/11/2022]. See the T
LodzUniversityofTechnology erm
ICZ9PPU̇n0roehnos-lref9tiao.vim2ntmLeu4duristsscLektairotioyyeDdfgeozGolfl’eAP1nm1ae6dircoaovlaandEcological BAfBtTtrhhirhobeiictsemlaiDispoDtheatguheulrLboutaeilsgbpticBuscrhhcaareiehircttyrieiNoiesnCncNahfaotoaitiLrrnoatdmiinlbootfaahrngoltaebuariroiliDytbnbnh.lgieiipbo-usuilttnibbhso-olcetPiohhksuhkeebeklidiscliaabstvytisaoinlaDbaleta s and Conditions (https://onlinelibrary.w
DVieapMaratmrzeonloto1fChemicalSciences Ndaattaioanrealabvibaliiloabgrleafioen;tdheetaIinletedrnbiebtlaiotgraphic iley.com
53131Padova <http://dnb.d-nb.de>. /term
ICtoavleyrImage:©alice-photo/Shutterstock ©6A9l4l260ri92g3hWWtseiIrnLehsEeeYrimv-Ve,dCGH(einrGmclmuandbiyHn,gBthosocshesotrfaße12, s-and-conditions) on W
translationintootherlanguages).Nopartof iley O
thisbookmaybereproducedinanyform–by nline L
pmmftrrhoaeaodmactehnomtisphnr–aeeirnnpklatousin,rnbgegtlurti,scaamh.nguesiercsmsrew.oidtiRfittiehelnmdgotiuo,hsttorieswrtrrbearaodinntoytnsekloana,tmtehpeveedeesrrni,mnwtioshsaieonn ibrary for rules of use; O
ncPeeoTyoPPBroipnuDotnebsotFssipkIdIeISSeSteIBBStcBriiNBNenNfidN:g::c99:9au7797lnl8S878yp-t-8-3r3r3m-ao--3-55i5ta-v2e252rec77k27,t--7e-e3C88d-d5383h1a232be2s221yn6029snl--u1-a80a4-cwi7h,.I,nadreianottobe A articles are governed by the applicable C
reative C
om
m
ons L
icense
D
ow
nloaded from
https://onlinelibrary.w
iley.com
Dedicatedto /doi/ by ibrahim
ProfessorDavidW.C.MacMillanandProfessorBenjaminListfortheir ragab - C
oaurotsutnadndthinegwcoornldtriwbhuotiocnonsttroibthuetefidetlodtohfeofirgealdnoocfaotraglaynsioscaantadlytosisalmltahkeinregsietasrucchherasn ochrane G
inspirationalandmeaningfulareaofresearch erm
any , W
InmemoryofProfessorCarlosF.BarbasIII(1964–2014)whopassedawaytoosoon iley O
nline L
ibrary on [23/11/2022]. See the T
erm
s and C
onditions (https://onlinelibrary.w
iley.com
/term
s-and-conditions) on W
iley O
nline L
ibrary for rules of use; O
A
articles are governed by the applicable C
reative C
om
m
ons L
icense
D
ow
nloaded from
vii https://onlinelibrary.w
iley.com
/doi/ by ibrahim
ragab - C
Contents ochrane Germ
any , W
iley O
Volume1 nline L
PParerftaIce NAxseiyiwimCmaetatrlyicstOsragnadnoAccattiavalytsioisnS1trategiesin ibrary on [23/11/2022]. See the T
1 NewDevelopmentsinEnantioselectiveBrønstedAcid erm
CatalysiswithStrongHydrogenBondDonors 3 s and C
1111....4312 CCICCnahhhtriiriorrrolaaaidnlllueCBBcIIyDtNNicoolSOronsApLc-eh-APn3ahmtnaoddmsipCeohnhnoyriiurls-imtBcoaApSshcaeidlSdtcssBhirnnø9enDidseteehrdydArcaitdiosnR1e2actions 5 onditions (https://onlinelibrary.w
11..56 CDoismulbfionneidmTidheisour1e6a-CarboxylicAcids 14 iley.com
1111....78910 SIISmmiulymiiddlimoouddmaiirppyAhhaoosnyssmhpdhoCmrooirecnitmArcilcciudiCsdaistooeunsns1t9e2r35i7on-DirectedCatalysis 29 /terms-and-conditions) on W
Acknowledgments 37 iley O
References 37 nline L
22.1 IAOCnazrtugtrasaolandyoKsuisocsutnipdoeo4nrh3baa4ns3edsM–aMsaohviriongTeBraedyoandClassicalBrønstedBase ibrary for rules of use; O
A
222222......245673 CCCOSCRuehhhhthmfiiiierrrreraaaamrellllCnaCPHTrch1ryyieiig-casrPahlaronhyelpdolr6Sir-sm5tCoOprpoohirnendnanoegzcpirelmBuhnPrsoeihøinsoonCepnssahCpstteohaadrlatay6azBns4leytaensssCetesaCC5t2aaa4ttlaya6lslyytsssttss485682 articles are governed by the applicable Creative C
om
m
ons L
icense
D
ow
nloaded from
viii 3Contents AApsypmlicmaetitorincsPthoaNsee-wTrCaonnsfceerpCtsata7ly1sis–FromClassical https://onlinelibrary.w
3.1 IJanntrOodteuvcrteiloannd7M1arioWaser iley.com
33..22.1 CChlaisrsaelsCoaftiAosny-mBamseedtrCicaPtaTlCyssts 7374 /doi/ by ibrahim
33..22..23 CUhnicrhaalrAgnedioPnT-BCassed8C0atalysts 78 ragab - C
33..33.1 “ACplpalsisciactailo”nAspopflCichaitriaolnPsToCfsQu8a1ternary(Amm)-OniumSalts 82 ochrane Germ
3.3.2 SNArReactions 83 any , W
3.3.3 UmpolungofImines 84 iley O
3333333.......3333333.......15679840 AIIUPEUnnTlmttettiiCerllcmaiirt-zzmmrCaaooottnoopiinllooiheeutnniccrmlouuiooclllffl(aaαeHOArrd-Hly-CCl,RpeaaeNeonrrtae)-bbo,-crooaIoato-t-infevdaausdiinnnttySddec-8toCHHNi6foaueeFntttca+aeelllrreyiaoozosnccaipdsyythiccoFillliin−1ezzs0aaRS5ttpeiiooea9nncc4iteAAiosppnppsrr1oo0aa91cc9hheess 8897 nline Library on [23/11/2022]. See the T
33..33..1112 PBTisCgusainniCdoinmiubminaStailotn-CwatitahlyPzhedotOocxhideamtiiosntrsyUs1in06gPermanganate, erms and C
33..33..1123.1 PTRSyTuenfnCeogsrpseitsnnaisctCeeso1m10b1080i7n9ationwithTransitionMetalCatalysis 108 onditions (https://onlinelibrary.w
4 EAsstyembamneMtraictaIdoonr-,PRaoisrianrgioaFnedrnHá-nBdoenz,dJionsgéCMa.tLaalysssiaslett1a2,1andDavidMonge iley.com
4444....1222..12 RRIInoeentaar-ccoPttdaiioouirnncwtssioIIinntnhvvooCll1hvv2iiinn1ragglONCxiatytragolegynesn-tS--BtSaotbauibnliidlziezSdepdCecCattaaitotionornsAsn1i21o22n6s 122 /terms-and-conditions) on W
4.2.3 ReactionsNotInvolvingHeteroatom-StabilizedCarbocations 132 iley O
444444......333444....2112 ICCMMAoaanneettirr-aaoggPllniiyyann-ssiBrggtt--iwBBAAnooidnntuuihiinoonnCgnndd-hCBBOAiairinxnntayaidldo-liCAiynnnsalggiAltsyawwclCltyiCiiottnshhamtg-tABiNbaooimsunnuNceiAnlndeudcoocwtcRpliaenihettoghaaiplclaihyOctsisivtCliEhesealeeItrcao11tAlnry43socs04tipishv1ai3lt1ei4o3n71M36odes 137 nline Library for rules of use; OA
4455...145.3 MISRISAsnuyleoaetnmftrsrethotgrhmadiieoeniunrausgcrcJiry.steAeiNsoaaninnm1Ciod51amn14tC1ao4Bo5l,yi1nCnsclidalsuiinr–segioNMwne.siwYthoOu1Pnp4hgp3o,otaorntcudhneAimtnideicrseafwloArDcA.tsSivymamtitimhonestric142 articles are governed by the applicable Creative C
om
m
ons L
icense
D
ow
nloaded from
55..22.1 AAccyyllaTtirvaensKfeinreRtiecaRcteiosonlsutio1n54sofAlcohols 154 Contents ix https://onlinelibrary.w
55..22..23 ANc-AylcaytliavteioDnesy1m5m9 etrizationofDiols 158 iley.com
55..22..45 KDiynneatmiciRceKsionluettiiconRseosoflCuhtiiornalsCa1r6b2oxylicAcidDerivatives 161 /doi/ by ibrahim
55..23.6 ESinlyalnTtiroasneslfeecrtiRveeaOct–iConAscy1l6T5ransfer 163 ragab - C
55..44.1 Mα,βic-UhaneslaAtudrdaitteidonA-AcynlnAumlamtioonnium166Intermediates 166 ochrane Germ
5.4.2 CascadeReactions 170 any , W
5.4.3 Cycloadditions 174 iley O
5555555.......4556578...421 CCCSDSSuouaa(i1alrmttifaas)da-tmll-AeyycSressamuettrMopyTTm-puuoaaoodrrnnnrnnidtdfiiooeuCcvvdEmaeeonCtrrniaEaobbcntnnyylatuoilAAsoylaissrr1otieyy8esnlll0seooscxxt1iiidd191vee70e973[211,378]51-SigmatropicRearrangements 188 nline Library on [23/11/2022]. See the T
erm
References 193 s and C
666..12 IXMHAnsaBitkylrokmDogdKomeuanneaco-ttsrBriisoikocnanaSsndyOdin2nrtT0ggh3õaeOnnsrioisgscaKanato2na0lcgya3estrtaslys2is04–NewOpportunitiesfor onditions (https://onlinelibrary.w
6.3 SolelyXBCatalyticActivationinCombinationwithAsymmetric iley.com
Counterion-DirectedCatalysis 207 /term
666...645 TABinoisfpAyuimnscyscmmtRieometnlraeiacttlerCCidcaatCttoaaalAlytyasssliytyssmstaihmsnrdoetu2Crg1ioch1-XCSBaotlCaellayyttaXiclBySsCyissatteam2ly1st5iUctAilciztiivnagtiXoBnAc2t0i9vation s-and-conditions) on W
6.7 FuturePerspectives 217 iley O
6.8 SummaryandConclusions 219 nline L
7 RMAseeyfremgriemnngecteOrsircgSa2yn2no0tchaetasilsysis2w25ithLight–NewOpportunitiesfor ibrary for rules of use; O
A
777777......212222....1112..21 DDDAICJonomuuustévraaaioalllnAldCCAeeluensaammctttataaiáCisnllonyyOaen,sst-riiLaPssgelh::ayy2IEonsr2meitno5soai-MrnPmeaih2durio2onzmt7oxeo,--CcBJBoaaaasttsaseaeellydAdys.sStSiFststerrarantt22eeá3g2gn5y8ydez22-S32a38las,andAlbertoFraile articles are governed by the applicable C
7.2.2.1 EnaminePhoto-Organocatalysis 235 reative C
om
m
ons L
icense