Ethyl diazoacetate → 4-(Tert-butyl-diphenyl-silanyloxy)-bicyclo[5.1.0]octane-8-carboxylic acid ethyl ester
Reaction equation
[C:1]([Si:5]([O:18][CH:19]1[CH2:25][CH2:24][CH:23]=[CH:22][CH2:21][CH2:20]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[N+](=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N-]>ClCCl>[CH2:32]([O:31][C:29]([CH:28]1[CH:22]2[CH:23]1[CH2:24][CH2:25][CH:19]([O:18][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:20][CH2:21]2)=[O:30])[CH3:33]Participants
4
Procedure
To a solution of Example 8C (2.2 g, 6.28 mmoles) and Rh2(OAc)4 (2 mg, 4.3 μmol) in dichloromethane (2 mL), ethyl diazoacetate (0.717 g, 6.28 mmoles) in dichloromethane (4 mL) was added over two hours via a syringe pump. The solvent was evaporated in vacuo and product purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 80:20) to provide the title compound.