Synthesis and applications of chiral ligands based on the bicarbazole skeleton

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Botman, P.N.M.

Publication date

2004

Link to publication

Citation for published version (APA):

Botman, P. N. M. (2004). Synthesis and applications of chiral ligands based on the

bicarbazole skeleton.

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LISTT OF ABBREVIATIONS [a] ] Ac c acac c APT T Av v Bn n b.p. . brr s "Bu u 'Bu u c c °C C calcd d COD D c

>' '

s s

d d DABCO O dba a de e DDQ Q DHB B DIBAL-H H DIPEA A DMAP P DMF F DMSO O d p p b b dppe e dppf f EDC C ee e EE E EI I ES S Et t equiv v FAB B S S GC C h h HOBt t specificc rotation acetyl l acetylacetonate e

attachedd proton test (in NMR) average e

benzyl l boilingg point

broadd signal (in NMR)

normal-butyi normal-butyi ff erf-butyl concentration n degreess Celsius calculated d 1,5-cyclooctadiene e cyclohexyl l

chemicall shift in parts per million doublett (in NMR) 1,4-diazabicycloo [2.2.2] octane trans,trans, frans-dibenzylideneacetone diastereomericc excess 2,3-dichloro-5,6-dicyano-l,4-benzoquinone e 2,5-dihydroxybenzoicc acid diisobutylaluminumm hydride diisopropylethylamine e 4-dimethvlaminopyridine e N,JV-dimethylformamide e dimethylsulfoxide e 1,4-diphenylphosphinobutane e 1,2-diphenylphosphinoee thane l,l'-bis(diphenylphosphino)ferrocene e l-(3-dimethylaminopropyl)-3-ethylcarbodiimide e enantiomericc excess ethoxyethyll ether electronn impact (in MS) electronn spray (in MS) ethyl l

equivalent t

fastt atom bombardment (in MS) gram(s) )

gass chromatography hour(s) )

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HRMS S HPLC C H M D S S HMPT T Hz z IR R ƒ ƒ L L m m MALDI-TOF F Me e min n M.p. . MS S nbd d NMR R Nf f PE E P-P-Ph h p p m m PPTS S 'Pr r Rf f rt t s s S S t t T T TBAF F TBS S TFAA A THF F TLC C Tf f TMS S to! ! tR R Ts s q q V V xyl l

highh resolution mass spectrometry highh pressure liquid chromatography hexamethyldisilazane e hexamethylphosphorouss triamide Hertz z infrared d couplingsconstantt (in NMR) liter(s) ) multiplett (in NMR)

matrixx assisted laser desorption ionization time-of-flight (in methyl l

minute(s) )

meltingg point/ range masss spectrometry 2,5-norbornadiene e

nuclearr magnetic resonance nonafluorobutanesulfonyl l petroleumm ether (60-80)

para--phenyl l

partss per million

pyridiniumm p-toluenesulfonic acid ('so-propyl l

retentionn factor (on TLC) roomm temperature singlett (in NMR) solvent t triplett (in NMR) temperature e tetrabutylammoniumm fluoride frrf-butyldimethylsilyl frrf-butyldimethylsilyl trifluoroaceticc acid anhydride tetrahydrofuran n

thinn layer chromatography trifluoromethanesulfonyl l trimethylsilyl l

toluene e

retentionn time (in chromatography) p-toluenesulfonyl l

quartett (in NMR) volume e

xylyl l