2,6-Lutidine → HCID 178444628, compound

HRID 1812618Notes

Reaction equation

HRID 1812618 reaction equation
C#CCCCCC=O.Cc1ccc(C(=O)CBr)cc1>C[Si](C)(C)OC(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)[C@H]1CCCN1.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(C)cc1.C#CCCC[C@H](C=O)CC(=O)c1ccc(C)cc1

Participants

8

Reactant 3

HCID 79372,6-LutidineHCID 692722-Bromo-4'-methylacetophenoneHCID 11355455Hept-6-ynal

Product 2

HCID 178444628HCID 178444628, compoundHCID 178444629HCID 178444629, compound

Reagents, catalysts & solvents 3

HCID 16218311(R)-alpha,alpha-Bis(3,5-bis(trifluoromethyl)phenyl)-2-pyrrolidinemethanol trimethylsilyl etherCatalystHCID 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-f2b4f06feedf48dc9d1e6f78cfe8cdf2
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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