Synthesis and characterization of a chiral Zn(II) complex based on a trans-1,2-diaminocyclohexane derivative and catalytic reduction of acetophenone

Reaction of ZnCl 2with R, R-bmbcd (= N, N ′-bis(4-methoxy-benzyl)-cyclohexane-1,2-diamine) yields the chiral [ZnCl 2( R, R-bmbcd)] in which the Zn atom has a distorted tetrahedral geometry involving two nitrogen atoms of R, R-bmbcd and two chloro ligands. The catalytic enantioselective reduction of...

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Bibliographic Details
Published in:Polyhedron 2004-07, Vol.23 (12), p.2063-2067
Main Authors: Roh, Soo Gyun, Yoon, Jong Uk, Jeong, Jong Hwa
Format: Article
Language:English
Subjects:
Catalytic enantioselective reduction
Crystal structure
trans-1,2-Diaminocyclohexane
Zinc complex
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Summary:Reaction of ZnCl 2with R, R-bmbcd (= N, N ′-bis(4-methoxy-benzyl)-cyclohexane-1,2-diamine) yields the chiral [ZnCl 2( R, R-bmbcd)] in which the Zn atom has a distorted tetrahedral geometry involving two nitrogen atoms of R, R-bmbcd and two chloro ligands. The catalytic enantioselective reduction of acetophenone promoted by R, R-bmbcd:Zn(OTf) 2=1:1 mole ratio in the presence of catecholborane give ( S)-(−)-1-phenylethanol in 48% ee with 77% yield. Reaction of ZnCl 2 with R, R-bmbcd (= N, N ′-bis(4-methoxy-benzyl)-cyclohexane-1,2-diamine) 1 in ethanol yields the chiral [ZnCl 2( R, R-bmbcd)] 2, which crystallizes in the monoclinic space group P2 1. The Zn atom has a distorted tetrahedral geometry involving two nitrogen atoms of R, R-bmbcd and two chloro ligands with the range of bond lengths, 2.066(2)–2.2289(9) Å. The result of the catalytic enantioselective reduction of acetophenone promoted by R, R-bmbcd:Zn(OTf) 2=1:1 mole ratio in the presence of catecholborane for 48 h at 0 °C give ( S)-(−)-1-phenylethanol in 48% ee with 77% yield.
ISSN:0277-5387
DOI:10.1016/j.poly.2004.04.033