HCID 23591231, compound → HCID 22259816, compound

HRID 1611072Notes

Reaction equation

HRID 1611072 reaction equation
[C:1]1([P@@:7]2(=[O:13])[CH2:11][CH2:10][CH2:9][C:8]2=[CH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)(Cl)Cl>[C:1]1([P:7]2(=[O:13])[CH2:11][CH2:10][CH2:9][C:8]2=[CH2:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 23591231HCID 23591231, compound

Product 1

HCID 22259816HCID 22259816, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Phenyl-2-methylenephospholane-1-oxide (3.0 g, chemical purity ca. 80%) was separated by repeated injections on a CHIRALPAK® AD 20 μm column (250×50 mm; mobile phase 100% acetonitrile, flow rate 120 ml/min) to afford 0.9 g of (S)-1-phenyl-2-methylenephospholane-1-oxide (ee 100%, chemical purity 95%; [α]D=−99.6 (c=1.03, CHCl3) and 1.0 g of (R)-1-phenyl-2-methylenephospholane-1-oxide (ee 99.4%, chemical purity 99.5%; [α]D=+106.8 (c=1.00, CCHCl3).

Sources & evidence

ORD record
ord-f4525544a8474ebab9d69164c21fc439
Source dataset
uspto-grants-2006_01
Patent number
US06984744B2

Reaction notes

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