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404454 - (S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride

404454 Aldrich

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

Synonym: (S,S)-Jacobsen’s catalyst

CAS Number 135620-04-1
Linear Formula [[[(CH₃)₃C]₂C₆H₂-2-(O-)CH=N]₂C₆H₁₀]MnCl
Molecular Weight 635.20
MDL number MFCD02101663
PubChem Substance ID 24865247
Popular Documents: Specification Sheet (PDF) | FTIR (PDF)

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

Properties

Related Categories	Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Epoxidation, Fluorination Catalysts, Fluorination Reagents, Privileged Ligands and Complexes, SALENs, Synthetic Reagents More...
mp	330-332 °C(lit.)

Description

Application

Salen (Mn)-catalyzed asymmetric epoxidation of unfunctionalized olefins.^6,^7,^8,⁹ High enantioselectivities and yields are obtained for a variety of substrates,⁶ especially cis-alkenes. A few applications include the synthesis of the taxol side chain¹⁰ and cis-1-amino-2-indanol.^11,¹² Jacobsen′s catalyst has also been used in the asymmetric α-hydroxylation of silyl enol ethers.¹³ Catalyst for the enantioselective epoxidation of a variety of olefins.^13,¹⁴

Reactant involved in:
• Studies of intercalative binding with ct-DNA and radical scavenging antioxidant activity¹
• Immobilization on phenoxy-modified zirconium poly(styrenephenylvinylphosphonate)²
• Synthesis of derivatvies for studies of conformational models of enantioselective reactions³

Catalyst involved in:
• Asymmetric epoxidation of olefins⁴
• Immobilization on ionic liquid modified mesoporous silica for oxidative kinetic resolution of racemic secondary alcohols†
• Immobilization on diamine modified zirconium olig-styrenyl phosphonate hydrogen phosphate for epoxidation of styrene⁵

Packaging

1, 5, 25 g in glass bottle

Legal Information

Manufactured under license by Shasun Chemicals and Drugs Limited, using Jacobsen HKR technology.

Price and Availability

Related Papers

1. Influence of chirality using Mn(III) salen complexes on DNA binding and antioxidant activity N. H. Khan, et al., Org. Biomol. Chem. 8, 4297-4307, (2010)

Technical information & documentation associated with this product is available in the Safety & Documentation tab.

Papers

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1. Influence of chirality using Mn(III) salen complexes on DNA binding and antioxidant activity N. H. Khan, et al., Org. Biomol. Chem. 8, 4297-4307, (2010)

2. Highly Enantioselective Epoxidation of Unfunctionalized Olefins Catalyzed by Chiral Jacobsen's Catalyst Immobilized on Phenoxy-Modified Zirconium Poly(styrene-phenylvinylphosphonate)phosphate X. Zou, et al., Adv. Synth. Catal. 352, 163-170, (2010)

3. Chiral Distortion in a MnIV(salen)(N3)2 Derived from Jacobsen's Catalyst as a Possible Conformation Model for Its Enantioselective Reactions T. Kurahashi and H. Fujii, Inorg. Chem. 47, 7556-7567, (2008)

4. Synthesis of a new type of immobilized chiral salen Mn(III) complex as effective catalysts for asymmetric epoxidation of unfunctionalized olefins B. Gong, et al., J. Catal. 262, 9-17, (2009)

5. Chiral Salen Mn(III) complex axial coordination immobilized on diamine modified ZSPP and their catalytic epoxidation of styrene R. Bai, et al., Catal. Commun. 9, 1588-1594, (2008)

6. W. Zhang et al. J. Am. Chem. Soc. 112, 2801, (1990)

7. Zhang, W. Jacobsen, E.N. J. Org. Chem. 56, 2296, (1991)

8. E.N. Jacobsen et al. J. Am. Chem. Soc. 113, 7063, (1991)

9. Lee, N.H. et al. Tetrahedron Lett. 32, 5055, (1991)

10. L. Deng, E.N. Jacobsen J. Org. Chem. 57, 4320, (1992)

11. Senanayake, C.H. et al. Tetrahedron Lett. 37, 3271, (1996)

12. Senanayake, C.H. et al. Tetrahedron Lett. 36, 3993, (1995)

13. Adam, W. et al. Tetrahedron 37, 6531, (1996)

14. J. Am. Chem. Soc. 113, 7063, (1991)

A chiral Mn(III) salen complex immobilized onto ionic liquid modified mesoporous silica for oxidative kinetic resolution of secondary alcohols S. Sahoo, et al., Tetrahedron Lett. 49, 4865-4868, (2008)

FT-IR 2 (3), 4564:B / Structure Index 1, 493:C:8

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Signal word	Warning
Hazard statements	H315-H319-H335
Precautionary statements	P261-P305 + P351 + P338
Personal Protective Equipment	dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes (Europe)	Xi
Risk Statements (Europe)	36/37/38
Safety Statements (Europe)	26-36
WGK Germany	3

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