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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

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About This Item

Linear Formula:
[[[(CH3)3C]2C6H2-2-(O-)CH=N]2C6H10]MnCl
CAS Number:
138124-32-0
Molecular Weight:
635.20
MDL number:
MFCD02101664
UNSPSC Code:
12352101
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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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)
Senanayake, C.H. et al.
Tetrahedron Letters, 36, 3993-3993 (1995)
Zhang, W. Jacobsen, E.N.
The Journal of Organic Chemistry, 56, 2296-2296 (1991)
Adam, W. et al.
Tetrahedron, 37, 6531-6531 (1996)
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