2,6-Lutidine → HCID 178444628, compound

HRID 1812640Notes

Reaction equation

HRID 1812640 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.[Ru++].F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.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(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 15198703Tris(2,2'-bipyridine)ruthenium(II) Bis(hexafluorophosphate)CatalystHCID 16218311(R)-alpha,alpha-Bis(3,5-bis(trifluoromethyl)phenyl)-2-pyrrolidinemethanol trimethylsilyl etherCatalystHCID 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-d5c2cd27d0c84b499261d8a377807e64
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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