2,6-Lutidine → HCID 178444640, compound

HRID 1813728Notes

Reaction equation

HRID 1813728 reaction equation
C#CCCCCC=O.FC(F)(F)Oc1ccc(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.F[P](F)(F)(F)(F)F.CC(C)(C)C1=CC=[N@H]2C(=C1)C3=CC(=CC=[N@@H]3[Ir]2456c7cc(F)cc(F)c7C8=CC=C(C=[N]48)C(F)(F)F)C(C)(C)C.Fc9cc(F)c(C%10=[N]5C=C(C=C%10)C(F)(F)F)c6c9.CN(C)C=O.Cc1cccc(C)n1>C#CCCC[C@@H](C=O)CC(=O)c1ccc(OC(F)(F)F)cc1.C#CCCC[C@H](C=O)CC(=O)c1ccc(OC(F)(F)F)cc1

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 27786912-Bromo-1-[4-(trifluoromethoxy)phenyl]ethan-1-oneHCID 11355455Hept-6-ynal

Product 2

HCID 178444640HCID 178444640, compoundHCID 178444641HCID 178444641, compound

Reagents, catalysts & solvents 2

HCID 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-902d39466e16431ba9b2b6b8c8ff6b0f
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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