On-Step Synthesis of a Bifunctional BINOL Ligand for the Highly Enantioselective Cyanation of Aliphatic Aldehydes

An efficient one-step synthesis of the optically active bifunctional BINOL ligand (S)-3 has been developed. It was found that (S)-3 in combination with Me2AlCl is a highly enantioselective catalyst for the addition of TMSCN to aliphatic aldehydes of diverse structures and is also among the most prac...

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Bibliographic Details
Published in:Organic letters 2005-06, Vol.7 (12), p.2381-2383
Main Authors: Qin, Ying-Chuan, Liu, Lan, Pu, Lin
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Catalysis
Combinatorial Chemistry Techniques
Cyanides - chemical synthesis
Cyanides - chemistry
Ligands
Molecular Structure
Naphthols - chemistry
Stereoisomerism
Trimethylsilyl Compounds - chemistry
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Summary:An efficient one-step synthesis of the optically active bifunctional BINOL ligand (S)-3 has been developed. It was found that (S)-3 in combination with Me2AlCl is a highly enantioselective catalyst for the addition of TMSCN to aliphatic aldehydes of diverse structures and is also among the most practical ones. A remarkable positive nonlinear effect was found for this chiral ligand.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050660e