2-Cyclopenten-1-one → (S)-3-(4-Bromophenyl)cyclopentan-1-one

HRID 2276831Notes

Reaction equation

HRID 2276831 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](OB(O)O)=[CH:4][CH:3]=1.[C:12]1(=[O:17])[CH2:16][CH2:15][CH:14]=[CH:13]1>C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:14]2[CH2:15][CH2:16][C:12](=[O:17])[CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 135882-Cyclopenten-1-oneHCID 3155134-Bromophenyl-boric acid

Product 1

HCID 25002103(S)-3-(4-Bromophenyl)cyclopentan-1-oneYield 91.3%

Reagents, catalysts & solvents 1

HCID 634876Binap, (A+-)-Catalyst

Procedure

4-Bromophenylboric acid (3.61 g, 18 mmol), cyclopentenone (0.50 mL, 6.0 mmol) and (S)-BINAP (224 mg, 0.36 mmol) were used and treated in a similar manner to (Step 1) of (Example 1) to give the title compound (1.31 g, 90%).

Workup

  1. additiontreated in a similar manner to (Step 1) of (Example 1)

Sources & evidence

ORD record
ord-2755166f682548b584e3764bb02e3e5b
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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