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Catalytic enantioselective cyanosilylation of ketones: improvement of enantioselectivity and catalyst turn-over by ligand tuning

โœ Scribed by Yoshitaka Hamashima; Motomu Kanai; Masakatsu Shibasaki

Book ID
104211583
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
67 KB
Volume
42
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Sterical and electronical tuning of the bifunctional catalyst 1 afforded the improved catalyst 2, which promoted the cyanosilylation of ketones with higher enantioselectivity as well as with improved catalyst turn-over with a factor of up to 10. Thus, chiral quaternary a-hydroxynitriles were obtained with excellent ee (up to 94% ee) using 1 mol% of 2 in the case of aryl ketones and 2.5 mol% of 2 in the case of aliphatic ketones.

๐Ÿ“œ SIMILAR VOLUMES

Studies toward practical synthesis of (2
Studies toward practical synthesis of (20S)-camptothecin family through catalytic enantioselective cyanosilylation of ketones: improved catalyst efficiency by ligand-tuning
โœ Kazuo Yabu; Shuji Masumoto; Motomu Kanai; Dennis P. Curran; Masakatsu Shibasaki ๐Ÿ“‚ Article ๐Ÿ“… 2002 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 128 KB

Enantioselective catalyst efficiency for the synthesis of the camptothecin family was improved through ligand-tuning. Key intermediates of two convergent syntheses of camptothecin (Curran's intermediate and Corey's intermediate) were obtained in up to 10 g scale through the catalytic enantioselectiv