2,6-Lutidine → HCID 178444630, compound

HRID 1813167Notes

Reaction equation

HRID 1813167 reaction equation
C#CCCCCC=O.FC(F)(F)c1ccc(C(=O)CBr)cc1>C[C@@H]1[NH2+][C@@H](C(C)(C)C)N(C)C1=O.[O-]S(=O)(=O)C(F)(F)F.C1=CC=C([C-]=C1)C2=CC=CC=N2.C1=CC=C([C-]=C1)C2=CC=CC=N2.C1=CC=C([C-]=C1)C2=CC=CC=N2.[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 11388194Ir(ppy)3CatalystHCID 139247132(2R,5S)-2-tert-butyl-3,5-dimethylimidazolidin-1-ium-4-one;trifluoromethanesulfonateCatalystHCID 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-32fea7829d894246afa5bc8460ce6959
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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