Asymmetric organocatalytic synthesis of tertiary azomethyl … · 2017. 3. 7. · 1 Asymmetric...
Transcript of Asymmetric organocatalytic synthesis of tertiary azomethyl … · 2017. 3. 7. · 1 Asymmetric...
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Asymmetricorganocatalyticsynthesisoftertiaryazomethylalcohols:keyintermediatestowardsazoxycompoundsandα-hydroxy-β-aminoestersJoséA.Carmona,aGonzalodeGonzalo,bInmaculadaSerrano,b,AnaM.Crespo-Peña,aMichalŠimek,aDavidMonge,*,bRosarioFernández*,bandJoséM.Lassaletta*,a
InstitutodeInvestigacionesQuímicas(CSIC-US),C/AméricoVespucio49,
41092Sevilla(Spain),andDepartamentodeQuímicaOrgánica,
UniversidaddeSevilla,C/Prof.GarcíaGonzález,1,41012Sevilla(Spain)
[email protected]; [email protected];[email protected]
CONTENTS 1.NMRSpectra.......................................................................................................................................2
2.GCChromatograms...........................................................................................................................38
3.HPLCChromatograms.......................................................................................................................40
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2017
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1.NMRSpectra:1HNMR(CDCl3,500MHz)ofVIII:
13CNMR(CDCl3,125MHz)ofVIII:
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1HNMR(CD3OD,500MHz)of9a:
13CNMR(CD3OD,125MHz)of9a:
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1HNMR(CD3OD,500MHz)of10a:
13CNMR(CD3OD,125MHz)of10a:
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1HNMR(CDCl3,400MHz)ofIX:
13CNMR(CDCl3,100MHz)ofIX:
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1HNMR(CDCl3,500MHz)ofX:
13CNMR(CDCl3,125MHz)ofX:
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1HNMR(CDCl3,500MHz)ofXI:
13CNMR(CDCl3,125MHz)ofXI:
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1HNMR(CDCl3,400MHz)ofXII:
13CNMR(CDCl3,100MHz)ofXII:
O
OBz
HN
BzO
BzO
OBz
HN
S
XII
CF3
CF3
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1HNMR(CDCl3,300MHz)ofXIII:
13CNMR(CDCl3,75MHz)ofXIII:
O
OPiv
HN
PivO
PivO
OPiv
HN
S
XIII
CF3
CF3
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1HNMR(CDCl3,400MHz)of[(S)-3a]:
13CNMR(CDCl3,100MHz)of[(S)-3a]:
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1HNMR(CDCl3,400MHz)of[(S)-3b]:
13CNMR(CDCl3,100MHz)of[(S)-3b]:
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1HNMR(CDCl3,300MHz)of[(S)-3c]:
13CNMR(CDCl3,125MHz)of[(S)-3c]:
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1HNMR(CDCl3,400MHz)of[(S)-3d]:
13CNMR(CDCl3,100MHz)of[(S)-3d]:
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1HNMR(CDCl3,300MHz)of[(S)-3e]:
13CNMR(CDCl3,75MHz)of[(S)-3e]:
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1HNMR(CDCl3,400MHz)of[(S)-3f]:
13CNMR(CDCl3,100MHz)of[(S)-3f]:
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1HNMR(CDCl3,400MHz)of[(S)-3g]:
13CNMR(CDCl3,100MHz)of[(S)-3g]:
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1HNMR(CDCl3,400MHz)of[(S)-4a]:
13CNMR(CDCl3,100MHz)of[(S)-4a]:
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1HNMR(CDCl3,500MHz)of[(S)-4b]:
13CNMR(CDCl3,125MHz)of[(S)-4b]:
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1HNMR(CDCl3,300MHz)of[(S)-4c]:
13CNMR(CDCl3,125MHz)of[(S)-4c]:
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1HNMR(CDCl3,400MHz)of[(S)-4d]:
13CNMR(CDCl3,100MHz)of[(S)-4d]:
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1HNMR(CDCl3,300MHz)of[(S)-4e]:
13CNMR(CDCl3,75MHz)of[(S)-4e]:
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1HNMR(CDCl3,400MHz)of[(S)-4f]:
13CNMR(CDCl3,100MHz)of[(S)-4f]:
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1HNMR(CDCl3,400MHz)of[(R)-4h]:
13CNMR(CDCl3,100MHz)of[(R)-4h]:
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1HNMR(CDCl3,400MHz)of[(R)-4i]:
13CNMR(CDCl3,100MHz)of[(R)-4i]:
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1HNMR(CDCl3,400MHz)of[(R)-4j]:
13CNMR(CDCl3,100MHz)of[(R)-4j]:
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1HNMR(CDCl3,300MHz)of[(R)-4k]:
13CNMR(CDCl3,75MHz)of[(R)-4k]:
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1HNMR(CDCl3,300MHz)of[(R)-4l]:
13CNMR(CDCl3,75MHz)of[(R)-4l]:
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1HNMR(CDCl3,300MHz)of[(S)-5a]:
13CNMR(CDCl3,75MHz)of[(S)-5a]:
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1HNMR(CDCl3,300MHz)of[(S)-5c]:
13CNMR(CDCl3,75MHz)of[(S)-5c]:
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1HNMR(CDCl3,300MHz)of[(S)-5d]:
13CNMR(CDCl3,75MHz)of[(S)-5d]:
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1HNMR(CDCl3,300MHz)of[(S)-5e]:
13CNMR(CDCl3,75MHz)of[(S)-5e]:
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1HNMR(CDCl3,400MHz)of[(S)-5f]:
13CNMR(CDCl3,100MHz)of[(S)-5f]:
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1HNMR(CDCl3,300MHz)of[(R)-5h]:
13CNMR(CDCl3,75MHz)of[(R)-5h]:
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1HNMR(CDCl3,300MHz)of[(R)-5i]:
13CNMR(CDCl3,75MHz)of[(R)-5i]:
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1HNMR(CDCl3,400MHz)of[(R)-5j]:
13CNMR(CDCl3,100MHz)of[(R)-5j]:
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1HNMR(CDCl3,300MHz)of[(R)-5k]:
13CNMR(CDCl3,75MHz)of[(R)-5k]:
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1HNMR(CDCl3,300MHz)of[(R)-5l]:
13CNMR(CDCl3,75MHz)of[(R)-5l]:
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2.GCChromatogramsGCconditionsfor3a:ChrompackCP7500,cyclodextrin-β,225mx0.25mmx0.25μm,Heasmobilephase
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GC conditions for (S)-3b: Chrompack CP7500, cyclodextrin-β, 225m x 0.25 mm x 0.25 µm, He as mobile phase
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3.HPLCChromatograms HPLCconditionsfor(S)-3c:ChiralpakAD-Hcolumn[hexane/i-PrOH(98:2)1mL/min]
HPLCconditionsfor(S)-3e:ChiralpakOJ-Hcolumn[hexane/iPrOH(98:2)1mL/min]
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HPLCconditionsfor(S)-4a:ChiralpakAD-Hcolumn[hexane/i-PrOH(98:2)1mL/min]
HPLCconditionsfor(S)-4b:ChiralpakOJcolumn[hexane/i-PrOH(98:2)1mL/min]
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HPLCconditionsfor(S)-4c:ChiralpakAD-Hcolumn[hexane/i-PrOH(98:2)1mL/min]
HPLCconditionsfor(S)-4d:ChiralpakAD-Hcolumn[hexane/i-PrOH(80:20)1mL/min]
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HPLCconditionsfor(S)-4e:ChiralpakOJ-Hcolumn[hexane/iPrOH(98:2)1mL/min]
HPLCconditionsfor(S)-4f:ChiralpakAD-Hcolumn[hexane/i-PrOH(80:20)1mL/min]
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HPLCconditionsfor(S)-4g:ChiralpakAD-Hcolumn[hexane/i-PrOH(80:20)1mL/min]
HPLCconditionsfor(R)-4h:ChiralpakAD-Hcolumn[hexane/i-PrOH(80:20)1mL/min]
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HPLCconditionsfor(R)-4i:ChiralpakAD-Hcolumn[hexane/i-PrOH(80:20)1mL/min]
HPLCconditionsfor(R)-4j:ChiralpakAD-Hcolumn[hexane/i-PrOH(80:20)1mL/min]
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HPLCconditionsfor(R)-4k:ChiralpakAD-Hcolumn[hexane/iPrOH(98:2)1mL/min]
HPLCconditionsfor(R)-4l:ChiralpakAD-Hcolumn[hexane/iPrOH(80:20)1mL/min]
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HPLCconditionsfor(S)-5a:ChiralpakAD-Hcolumn[hexane/iPrOH(80:20)1mL/min]
HPLCconditionsfor(S)-5c:ChiralpakAD-Hcolumn[hexane/iPrOH(80:20)1mL/min]
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HPLCconditionsfor(S)-5d:ChiralpakAD-Hcolumn[hexane/iPrOH(80:20)1mL/min]
HPLCconditionsfor(S)-5e:ChiralpakOJ-Hcolumn[hexane/iPrOH(90:10)1mL/min]
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HPLCconditionsfor(S)-5f:ChiralpakAD-Hcolumn[hexane/iPrOH(80:20)1mL/min]
HPLCconditionsfor(R)-5h:ChiralpakAD-Hcolumn[hexane/iPrOH(80:20)1mL/min]
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HPLCconditionsfor(R)-5i:ChiralpakIBcolumn[hexane/iPrOH(90:10)1mL/min]
HPLCconditionsfor(R)-5j:ChiralpakAD-Hcolumn[hexane/iPrOH(80:20)1mL/min]
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HPLCconditionsfor(R)-5k:ChiralpakIAcolumn[hexane/iPrOH(80:20)1mL/min]
HPLCconditionsfor(R)-5l:ChiralpakAD-Hcolumn[hexane/iPrOH(80:20)1mL/min]