2-Bromo-1-(4-hydroxyphenyl)ethanone → HCID 178444636, compound

HRID 1812851Notes

Reaction equation

HRID 1812851 reaction equation
C#CCCCCC=O.Oc1ccc(C(=O)CBr)cc1>CN1C(=O)[C@H](Cc2ccccc2)N[C@@H]1C(C)(C)C.COc1ccc(-c2cc(-c3ccc(OC)cc3)[o+]c(-c3ccc(OC)cc3)c2)cc1.[B-](F)(F)(F)F.CN(C)C=O.Cc1cccc(C)n1>C#CCCC[C@@H](C=O)CC(=O)c1ccc(O)cc1.C#CCCC[C@H](C=O)CC(=O)c1ccc(O)cc1

Participants

8

Reactant 3

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 79372,6-LutidineHCID 11355455Hept-6-ynal

Product 2

HCID 178444636HCID 178444636, compoundHCID 178444637HCID 178444637, compound

Reagents, catalysts & solvents 3

HCID 103098345-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone, (2S,5S)-CatalystHCID 110814222,4,6-Tris(4-methoxyphenyl)pyrylium tetrafluoroborateCatalystHCID 6228DimethylformamideSolvent5×

Conditions

Temperature
22 °C

Workup

  1. aliquot4 uL mixture of each reacted solution was collected and diluted with 36 uL ACN
  2. addition4 uL mixture of each reacted solution was collected and diluted with 36 uL ACN
  3. additionchiral resolving regent (150 mM in DCM, 40 uL)
  4. additionCuI with DIPEA (400 mM in ACN) 40 uL
  5. additioninternal standard 1-phenylprop-2-yn-1-ol (4) (25 mM in ACN) 40 uL
  6. stirringNo procedure recorded
  7. aliquotAfter the reaction, 10 uL of supernatant for each reaction was transferred to another 96-well plate
  8. additionAfter the reaction, 10 uL of supernatant for each reaction was transferred to another 96-well plate and diluted with 190 uL ACN before the IM-MS analysis

Sources & evidence

ORD record
ord-5eb07d109c1a4dc0afac2fa3e9818b44
Source dataset
Dataset from `Ultra-high-throughput mapping of the chemical space of asymmetric catalysis enables accelerated reaction discovery`

Reaction notes

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