Asymmetric NaBH4 1, 4‐Reduction of C3‐Disubstituted 2‐Propenoates Catalyzed by a Diamidine Cobalt Complex. Issue 10 (27th April 2015)

• Record Type: Journal Article
• Authors: Shuto, Yoshihiro; Yamamura, Tomoya; Tanaka, Shinji; Yoshimura, Masahiro; Kitamura, Masato
• Is Part Of: ChemCatChem. Volume 7:Issue 10(2015:May)
• Page Start: 1547
• Page End: 1550
• Publication Date: 2015-04-27
• Subjects: Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201500260
• Languages: English
• ISSNs: 1867-3880

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A new Co complex of a unique diamidine ligand catalyzes asymmetric NaBH₄ reduction of C3‐disubstituted (<italic>E</italic>)‐ and (<italic>Z</italic>)‐2‐propenoates, including C3‐oxygen‐ and nitrogen‐substituted substrates with high enantioselectivity. Analysis by X‐ray diffraction, ¹H NMR spectroscopy, ring‐opening radical‐clock and D‐labeling reactions, and the structure/selectivity relationship suggest that a mechanism of CoH‐involved non‐single‐electron transfer 1, 4‐addition differentiates the C2 enantioface. Involvement of CoH species has been supported by quantitative isolation of a new type of CoH₂(BH₃)₂ complex.</p> </abstract>