2,6-Lutidine → HCID 178444630, compound

HRID 1813183Notes

Reaction equation

HRID 1813183 reaction equation
C#CCCCCC=O.FC(F)(F)c1ccc(C(=O)CBr)cc1>O=C(O)[C@H]1CCCCN1.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)c1ccc(C(F)(F)F)cc1.C#CCCC[C@H](C=O)CC(=O)c1ccc(C(F)(F)F)cc1

Participants

8

Reactant 3

HCID 79372,6-LutidineHCID 3219792-Bromo-4'-(trifluoromethyl)acetophenoneHCID 11355455Hept-6-ynal

Product 2

HCID 178444630HCID 178444630, compoundHCID 178444631HCID 178444631, compound

Reagents, catalysts & solvents 3

HCID 736316Pipecolic acid, (+)-CatalystHCID 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-06c97be71ad24c0b97a32b98e56b27d4
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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