2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Phenylcyclohexanone
Reaction equation
[CH:1]1[CH2:6][CH:5]=[CH:4][CH2:3][CH:2]=1.C([C:9]1[C:15](=O)[C:14](Cl)=[C:13](Cl)[C:11](=[O:12])[C:10]=1C#N)#N>>[C:1]1([CH:10]2[CH2:9][CH2:15][CH2:14][CH2:13][C:11]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
3
Procedure
Rh2(S-DOSP)4-catalyzed decomposition of the cyclic vinyldiazoacetate 58 in the presence of 1,3-cyclohexadiene 40 resulted in the formation of the 1,4-cyclohexadiene 59 in 73% yield and 97% ee. The absolute configuration of compound 59 was determined by DDQ oxidation and ozonolysis to afford the 2-phenylcyclohexanone in a 56% yield. Found [α]26D=−17 (c=1.66, PhH). Lit. value: [α]24D=−113.5 (c=0.60, PhH), S-isomer. (Berti et al., J. Chem. Soc., pp. 3371-3377 (1971), which is hereby incorporated by reference.) Similarly, decomposition of the dienyldiazoacetate 60 in the presence of 1,3-cyclohexadiene 40 resulted in the formation of 61 (60% yield and 99% ee), in which both diene components have moved out of conjugation.
Sources & evidence
- ORD record
- ord-f2a83ecb82144eeda992410b8ae215c0
- Source dataset
- uspto-grants-2004_07
- Patent number
- US06762304B2
Reaction notes
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