Jacobsen's Catalyst
Title: Jacobsen's Catalyst
CAS Registry Number: 149656-63-3
CAS Name: (SP-5-13)-Chloro[[rel-2,2¢-[(1R,2R)-1,2-cyclohexanediylbis[(nitrilo-kN)methylidyne]]bis[4,6-bis(1,1¢-dimethylethyl)phenolato-kO]](2-)]manganese
Molecular Formula: C36H52ClMnN2O2
Molecular Weight: 635.20
Percent Composition: C 68.07%, H 8.25%, Cl 5.58%, Mn 8.65%, N 4.41%, O 5.04%
Literature References: Manganese-salen Schiff base complex used as a catalyst in asymmetric syntheses. Prepn: E. N. Jacobsen et al., J. Am. Chem. Soc. 113, 7063 (1991); large-scale: J. F. Larrow et al., J. Org. Chem. 59, 1939 (1994). Synthesis and enantioselectivity of dimer: K. B. M. Janssen et al., Tetrahedron: Asymmetry 8, 3481 (1997). HPLC determn of enantiomeric purity in commercial samples: J. Zukowski, Chirality 10, 362 (1998). Mechanism of asymmetric epoxidation of indenes: D. L. Hughes et al., J. Org. Chem. 62, 2222 (1997). Use in epoxidation of isoflavones: W. Adam et al., Tetrahedron: Asymmetry 9, 1121 (1998).
 
Derivative Type: (R,R)-form
CAS Registry Number: 138124-32-0
Additional Names: (R,R)-[N,N¢-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine]manganese (III) chloride
Properties: mp 324-326°. [a]D23 +580° (c = 0.01 in ethanol).
Melting point: mp 324-326°
Optical Rotation: [a]D23 +580° (c = 0.01 in ethanol)
 
Use: Chiral catalyst for epoxidation of olefins.

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