CAS 361346-80-7 (1R,2R)-N,N'-Bis(2-acetyl-3-oxo-2-butenylidene)-1,2-dimesitylethylenediaminato Cobalt(II)

Synonyms

361346-80-7;(1R,2R)-N,N'-Bis(2-acetyl-3-oxo-2-butenylidene)-1,2-dimesitylethylenediaminato Cobalt(II);(R)-AMAC;B2314;(1R,2R)-N,N'-BIS(2-ACETYL-3-OXO-2-BUTENYLIDENE)- 1,2-DIMESITYLETHYLENEDIAMINATO COBALT (II);

IUPAC Name

(E)-3-[[(1R,2R)-2-[[(E)-2-acetyl-3-oxidobut-2-enylidene]amino]-1,2-bis(2,4,6-trimethylphenyl)ethyl]iminomethyl]-4-oxopent-2-en-2-olate;cobalt(2+);

Molecular Weight

573.599g/mol

Molecular Formula

C32H38CoN2O4;

Canonical SMILES

CC1=CC(=C(C(=C1)C)C(C(C2=C(C=C(C=C2C)C)C)N=CC(=C(C)[O-])C(=O)C)N=CC(=C(C)[O-])C(=O)C)C.[Co+2];

InChI

InChI=1S/C32H40N2O4.Co/c1-17-11-19(3)29(20(4)12-17)31(33-15-27(23(7)35)24(8)36)32(34-16-28(25(9)37)26(10)38)30-21(5)13-18(2)14-22(30)6;/h11-16,31-32,35,37H,1-10H3;/q;+2/p-2/b27-23+,28-25+,33-15 ,34-16 ;/t31-,32-;/m1./s1;

InChI Key

PHCQQLMRNZRDJA-SGIDGJHMSA-L;

Complexity

846

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Defined Bond Stereocenter Count

Exact Mass

573.216g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

573.216g/mol

Rotatable Bond Count

Topological Polar Surface Area

105A^2

Application

The purpose of (1R,2R)-N,N'-Bis(2-acetyl-3-oxo-2-butenylidene)-1,2-dimesitylethylenediaminato Cobalt(II) is to serve as an efficient catalyst for the asymmetric borohydride reduction of carbonyl compounds. This Schiff base-cobalt complex is utilized for enantioselective borohydride reduction, facilitating the stereoselective preparation of aryl alcohols through the asymmetric reduction of aryl ketones with borohydride. Additionally, it enables the stereoselective reduction of diketones to produce diols, and supports the preparation of optically active deuterated primary alcohols via enantioselective borodeuteride reduction of aldehydes. Moreover, this catalyst plays a crucial role in the stereoselective preparation of β-hydroxy esters through dynamic kinetic resolution of alkylketo esters, and achieves chemoselective, diastereoselective, and enantioselective borohydride reduction of 1,3-diketones. Lastly, it is instrumental in the asymmetric synthesis of diarylhydroxypropanones by enabling stereoselective reduction of alkyldiaryldiketones.

March 4, 2025

Exceptional Catalyst for Asymmetric Reductions

Using the cobalt complex from Alfa Chemistry significantly enhanced our research on enantioselective reductions. Its efficiency in producing chiral alcohols with high selectivity makes it indispensable for our laboratory's synthetic chemistry projects.