Phenacyl bromide → HCID 178444626, compound

HRID 1812478

Reaction equation

HRID 1812478 reaction equation
C#CCCCCC=O.c1ccc(C(=O)CBr)cc1>O=C(O)[C@@H]1C[C@@H]2CCCC[C@@H]2N1.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)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 74084522-Carboxyoctahydroindole, (2S,3aS,7aS)-CatalystHCID 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-e1620a3a37534bbf891abb2e23e3f720
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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