Benzaldehyde → (R,R)-Stilbene oxide

HRID 1941477Notes

Reaction equation

HRID 1941477 reaction equation
[C:1]1([CH:7]=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H].[CH:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OC)(C)(C)C.ClCCl.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[CH:4]1[CH:3]=[CH:2][C:1]([C@H:7]2[O:19][C@@H:12]2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 136601Benzene, (diazomethyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 185583(R,R)-Stilbene oxideYield 5%

Reagents, catalysts & solvents 3

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of phenyldiazomethane (0.45 mmol in 6 ml of t-butylmethyl ether was added to a solution of a compound of formula (C') wherein R' and R" are both hydrogen (90 mg; 0.45 mmol), rhodium (II) acetate (2 mg; 0.0045 mmol) and benzaldehyde (46 μl; 0.45 mmol) in dichloromethane (2 ml). Upon completion of the addition, the solvent was removed in vacuo and the residue chromatographed using silica gel and elating with dichloromethane:petrol 40:60 to give the title compound (4 mg, 5%, 71%ee).

Workup

  1. additionUpon completion of the addition
  2. customthe solvent was removed in vacuo
  3. customthe residue chromatographed

Sources & evidence

ORD record
ord-8c5f22bc875a4d278e0a450db37cc256
Source dataset
uspto-grants-1997_12
Patent number
US05703246

Reaction notes

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