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(1S,2S)-(+)-[1,2-Cyclohexanediamino-N,N'-bis(3,5-di-t-butylsalicylidene)]chromium(III) chloride

(1S,2S)-(+)-[1,2-Cyclohexanediamino-N,N'-bis(3,5-di-t-butylsalicylidene)]chromium(III) chloride

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Catalog Number

ACM219143927-2

Product Name

Structure

CAS

219143-92-7

Product Overview
Usage
Reviews

Synonyms

SCHEMBL2189792;219143-92-7;(S,S)-N,N -Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminochromium(III) chloride;

IUPAC Name

chromium;2,4-ditert-butyl-6-[[(1S,2S)-2-[(3,5-ditert-butyl-2-hydroxyphenyl)methylideneamino]cyclohexyl]iminomethyl]phenol;chloride;

Molecular Weight

634.286g/mol

Molecular Formula

C36H54ClCrN2O2-;

Canonical SMILES

CC(C)(C)C1=CC(=C(C(=C1)C=NC2CCCCC2N=CC3=CC(=CC(=C3O)C(C)(C)C)C(C)(C)C)O)C(C)(C)C.[Cl-].[Cr];

InChI

InChI=1S/C36H54N2O2.ClH.Cr/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;/p-1/t29-,30-;;/m0../s1;

InChI Key

URIXSIRVKMNVQX-ARDORAJISA-M;

Complexity

800

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

EC Number

606-861-4

Exact Mass

633.328g/mol

Formal Charge

-1

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

633.328g/mol

Rotatable Bond Count

Topological Polar Surface Area

65.2A^2

Application

The compound (1S,2S)-(+)-[1,2-Cyclohexanediamino-N,N'-bis(3,5-di-t-butylsalicylidene)]chromium(III) chloride serves as a highly versatile catalyst in various chemical reactions, enhancing both the efficiency and specificity of these processes. It is primarily employed as a catalyst for the asymmetric ring-opening of meso-epoxides and in the kinetic resolution of terminal epoxides. Additionally, it acts as a precatalyst for both asymmetric Diels-Alder reactions and hetero Diels-Alder reactions. This compound further facilitates the copolymerization of CO2 with epoxides and is instrumental in the enantioselective alkylation of tributyltin enolates. Its utility extends to promoting the enantioselective addition of Me2Zn to aldehydes and the enantioselective intramolecular addition of tertiary enamides to ketones. The catalyst also supports asymmetric iodocyclization and catalytic intermolecular linear allylic C-H animation. Moreover, it functions as a cocatalyst for the enantioselective ring opening of epoxides with fluoride, making it an invaluable tool in advanced synthetic chemistry.

February 12, 2025

Outstanding Catalyst for Asymmetric Synthesis

I've used this product as a catalyst in asymmetric ring-opening of meso-epoxides. The results were impressive, providing high enantioselectivity. It's a game-changer for my research in catalytic processes. Highly recommend for any synthetic chemist!

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