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Hydroformylation in Natural Product Synthesis

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Hydroformylation for Organic Synthesis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 342))

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Abbreviations

Ac:

Acetyl

acac:

Acetylacetonate

aq:

Aqueous

B:L:

Branched:linear ratio

BDP:

Bisdiazaphospholane

BINAPHOS:

2-Diphenylphosphino-1,1′-binaphthalene-2,2′-diylphosphite

BIPHEPHOS:

6,6′-[(3,3′-Di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl- 2,2′-diyl) bis(oxy)]bis(dibenzo[d,f][1,3,2]dioxaphosphepin)

Bn:

Benzyl

Boc:

tert-Butoxycarbonyl

Bu:

Butyl

Bz:

Benzoyl

Cbz:

Benzyloxycarbonyl

CDG:

Catalyst directing group

cod:

Cyclooctadiene

conv:

Conversion

DBU:

1,8-Diazabicyclo [5.4.0]undec-7-ene

DCC:

N,N-Dicyclohexylcarbodiimide

DIBALH:

Diisobutylaluminum hydride

DMAP:

4-(Dimethylamino)pyridine

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

DMTMM:

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium

dr:

Diastereomer ratio

DuPHOS:

1,2-Bis[2,5-di-iso-propylphospholano]benzene

ee:

Enantiomer excess

gem :

Geminal

h:

Hour(s)

HFIP:

1,1,1,3,3,3-Hexafluoro-2-propanol

IBX:

2-Iodoxybenzoic acid

Ipc:

Isopinocampheyl

i-Pr:

Isopropyl

LiHMDS:

Lithium bis(trimethylsilyl)amide

m-CPBA:

m-Chloroperoxybenzoic acid

Me:

Methyl

mol:

Mole(s)

n-hept:

n-Heptyl

NMO:

N-Methylmorpholine-N-oxide

Nu:

Nucleophile

o-DPPB:

Ortho-diphenylphosphanylbenzoyl

PDC:

Pyridinium dichromate

PFL:

Pseudomonas florescens lipase

Ph:

Phenyl

PMP:

p-Methoxyphenyl

PPTS:

Pyridinium p-toluenesulfonate

Pr:

Propyl

pTSA:

p-Toluenesulfonic acid

Pv:

Pivaloyl

py:

Pyridine

rt:

Room temperature

TBAF:

Tetra-n-butylammonium fluoride

TBS:

tert-Butyldimethylsilyl

t-Bu:

tert-Butyl

Temp:

Temperature

TES:

Triethylsilyl

Tf:

Trifluoromethanesulfonyl (triflyl)

TFA:

Trifluoroacetic acid

THP:

Tetrahydropyran-2-yl or tetrahydropyran

TIPS:

Triisopropylsilyl

TMEDA:

N,N,N′,N′-Tetramethyl-1,2-ethylenediamine

TMS:

Trimethylsilyl

TPAP:

Tetrapropylammonium perruthenate

Tr:

Triphenylmethyl (trityl)

Ts:

Tosyl 4-toluenesulfonyl

XANTPHOS:

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

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Bates, R.W., Kasinathan, S. (2013). Hydroformylation in Natural Product Synthesis. In: Taddei, M., Mann, A. (eds) Hydroformylation for Organic Synthesis. Topics in Current Chemistry, vol 342. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2013_428

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