Practical synthesis of chiral ligands for catalytic enantioselective cyanosilylation of ketones

• Published in: Tetrahedron letters Vol. 43; no. 16; pp. 2919 - 2922
• Main Authors: Masumoto, Shuji, Yabu, Kazuo, Kanai, Motomu, Shibasaki, Masakatsu
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 15-04-2002
• Subjects: catalytic enantioselective reaction; chiral ligand; cyanosilylation; cyclic sulfate; ketones; ligand-tuning; practical synthesis; ligand-tuning; cyanosilylation; chiral ligand; ketones; catalytic enantioselective reaction; practical synthesis; cyclic sulfate
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(02)00450-1

A practical and more environmentally benign synthetic route of chiral ligands that are useful for catalytic enantioselective cyanosilylation of ketones is described. A key step is the regioselective S
N2 reaction to cyclic sulfate
12
with catechol derivatives. A range of chiral ligands containing electronically tuned catechols has become available by this new route.
A range of chiral ligands that are useful for catalytic enantioselective cyanosilylation of ketones was practically synthesized using a cyclic sulfate as a key intermediate.