2,6-Lutidine → HCID 178444632, compound

HRID 1813488Notes

Reaction equation

HRID 1813488 reaction equation
C#CCCCCC=O.Clc1ccc(C(=O)CBr)cc1>O=C(O)[C@H]1CCCN1.[H]O[H].[H]O[H].[H]O[H].[H]O[H].[H]O[H].[H]O[H].Cl[Ru]Cl.c1ccc(nc1)-c2ccccn2.c3ccc(nc3)-c4ccccn4.c5ccc(nc5)-c6ccccn6.CN(C)C=O.Cc1cccc(C)n1>C#CCCC[C@@H](C=O)CC(=O)c1ccc(Cl)cc1.C#CCCC[C@H](C=O)CC(=O)c1ccc(Cl)cc1

Participants

8

Reactant 3

HCID 79372,6-LutidineHCID 68303p-Chlorophenacyl bromideHCID 11355455Hept-6-ynal

Product 2

HCID 178444632HCID 178444632, compoundHCID 178444633HCID 178444633, compound

Reagents, catalysts & solvents 3

HCID 8988D-ProlineCatalystHCID 16211607Tris(2,2-bipyridyl)ruthenium(II) chloride hexahydrateCatalystHCID 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-feabf28ab8214b47a8e8c1df2ae099ea
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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