2,6-Lutidine → HCID 178444624, compound

HRID 1813089Notes

Reaction equation

HRID 1813089 reaction equation
C#CCCCCC=O.c2ccccc2c1ccc(C(=O)CBr)cc1>C[Si](C)(C)OC(c1ccccc1)(c1ccccc1)[C@@H]1CCCN1.C1=CC=C(C(=C1)C2=C3C=C(C(=O)C(=C3OC4=C(C(=C(C=C24)Br)O)Br)Br)Br)C(=O)O.[Na].[Na].CN(C)C=O.Cc1cccc(C)n1>C#CCCC[C@@H](C=O)CC(=O)c1ccc(-c2ccccc2)cc1.C#CCCC[C@H](C=O)CC(=O)c1ccc(-c2ccccc2)cc1

Participants

8

Reactant 3

HCID 79372,6-LutidineHCID 672821-(1,1'-Biphenyl)-4-yl-2-bromoethanoneHCID 11355455Hept-6-ynal

Product 2

HCID 178444624HCID 178444624, compoundHCID 178444625HCID 178444625, compound

Reagents, catalysts & solvents 3

HCID 11198150(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol Trimethylsilyl EtherCatalystHCID 124202469Eosin Y disodium salt, analytical standardCatalystHCID 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-71b14e0cdc304030b8b790c1dffa7bd0
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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