Phenacyl bromide → HCID 178444626, compound

HRID 1812461

Reaction equation

HRID 1812461 reaction equation
C#CCCCCC=O.c1ccc(C(=O)CBr)cc1>C1COCCN1.C1=CC=C([C-]=C1)C2=CC=CC=N2.C1=CC=C([C-]=C1)C2=CC=CC=N2.C1=CC=NC(=C1)C2=CC=CC=N2.F[P-](F)(F)(F)(F)F.[Ir+3].CN(C)C=O.Cc1cccc(C)n1>C#CCCC[C@@H](C=O)CC(=O)c1ccccc1.C#CCCC[C@H](C=O)CC(=O)c1ccccc1

Participants

8

Reactant 3

HCID 6259Phenacyl bromideHCID 79372,6-LutidineHCID 11355455Hept-6-ynal

Product 2

HCID 178444626HCID 178444626, compoundHCID 178444627HCID 178444627, compound

Reagents, catalysts & solvents 3

HCID 8083MorpholineCatalystHCID 54589530Iridium(3+);2-phenylpyridine;2-pyridin-2-ylpyridine;hexafluorophosphateCatalystHCID 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-f150d0e65e124a19b46c28b9166891cd
Source dataset
Dataset from `Ultra-high-throughput mapping of the chemical space of asymmetric catalysis enables accelerated reaction discovery`

Linked notes

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