Bromomethyl 4-methoxyphenyl ketone → HCID 178444638, compound

HRID 1812906Notes

Reaction equation

HRID 1812906 reaction equation
C#CCCCCC=O.COc1ccc(C(=O)CBr)cc1>CN1C(=O)[C@H](Cc2ccccc2)N[C@@H]1C(C)(C)C.FC1=CC([Ir]C2=C(C3=NC=CC=C3)C(F)=CC(F)=C2)=C(C4=NC=CC=C4)C(F)=C1.FC5=CC(F)=CC=C5C6=NC=CC=C6.CN(C)C=O.Cc1cccc(C)n1>C#CCCC[C@@H](C=O)CC(=O)c1ccc(OC)cc1.C#CCCC[C@H](C=O)CC(=O)c1ccc(OC)cc1

Participants

8

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 79372,6-LutidineHCID 11355455Hept-6-ynal

Product 2

HCID 178444638HCID 178444638, compoundHCID 178444639HCID 178444639, compound

Reagents, catalysts & solvents 3

HCID 103098345-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone, (2S,5S)-CatalystHCID 178505915HCID 178505915, compoundCatalystHCID 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-d8bd2856f2194f0fbc627f0e4c7c4155
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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