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Sigma-Aldrich

(R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride

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Synonym(s):
(R,R)-Jacobsen’s catalyst, Jacobsen’s catalyst
Linear Formula:
[[[(CH3)3C]2C6H2-2-(O-)CH=N]2C6H10]MnCl
CAS Number:
138124-32-0
Molecular Weight:
635.20
MDL number:
MFCD02101664
PubChem Substance ID:
24865246
NACRES:
NA.22

Quality Level

200

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Catalysis
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mp

330-332 °C (lit.)

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, Aligned

SMILES string

CC(C)(C)c1cc2\C=N\[C@@H]3CCCC[C@H]3\N=C\c4cc(cc(c4O[Mn](Cl)Oc2c(c1)C(C)(C)C)C(C)(C)C)C(C)(C)C

InChI

1S/C36H54N2O2.ClH.Mn/c1-33(2,3)25-17-23(31(39)27(19-25)35(7,8)9)21-37-29-15-13-14-16-30(29)38-22-24-18-26(34(4,5)6)20-28(32(24)40)36(10,11)12;;/h17-22,29-30,39-40H,13-16H2,1-12H3;1H;/q;;+3/p-3/b37-21+,38-22+;;/t29-,30-;;/m1../s1

InChI key

LJVAWOSDJSQANR-OHRASPNLSA-K

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General description

(R,R)-(-)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride is a metal-salen complex that can catalyze a variety of asymmetric transformations

(R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride is a catalyst used in the epoxidation of arenes.
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Application

Salen (Mn)-catalyzed asymmetric epoxidation of unfunctionalized olefins. High enantioselectivities and yields are obtained for a variety of substrates, especially cis-alkenes. A few applications include the synthesis of the taxol side chain and cis-1-amino-2-indanol. Jacobsen′s catalyst has also been used in the asymmetric α-hydroxylation of silyl enol ethers. Catalyst for the enantioselective epoxidation of a variety of olefins.

Legal Information

Manufactured under license by Sterling Pharma Solutions Limited, using Jacobsen HKR technology.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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A highly potential analogue of jacobsen catalyst with in-built phase transfer capability in enantioselective epoxidation of nonfunctionalized alkenes
Kureshy, Rukhsana I and Noor-ul, et al.
Chinese Journal of Catalysis, 209, 99-104 (2002)
Senanayake, C.H. et al.
Tetrahedron Letters, 36, 3993-3993 (1995)
Enantioselective arene epoxidation under mild conditions by Jacobsen catalyst: The role of protic solvent and co-catalyst in the activation of hydrogen peroxide
Rocha, Mariana, et al.
Applied Catalysis A: General, 460, 116-123 (2013)
Lee, N.H. et al.
Tetrahedron Letters, 32, 5055-5055 (1991)
Senanayake, C.H. et al.
Tetrahedron Letters, 37, 3271-3271 (1996)
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