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Catalytic enantioselective synthesis of (20s)-camptothecin intermediates using cyanosilylation of ketones promoted by D-glucose-derived lanthanide catalyst

Yabu, K and Masumoto, S and Kanai, M and Du, W and Curran, DP and Shibasaki, M (2003) Catalytic enantioselective synthesis of (20s)-camptothecin intermediates using cyanosilylation of ketones promoted by D-glucose-derived lanthanide catalyst. Heterocycles, 59 (1). 369 - 385. ISSN 0385-5414

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Abstract

An efficient catalytic enantioselective synthetic route was developed for Curran's versatile camptothecin intermediate (5). The key step is the catalytic enantioselective cyanosilylation of ketone (7) using a chiral samarium (Sm) complex. The target ketone cyanohydrin (6) was obtained with 90% ee using 2 mol % of the catalyst. A gadolinium (Gd) complex derived from the same chiral ligand could also be used as an enantioselective catalyst to synthesize Corey's intermediate (11).


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Yabu, K
Masumoto, S
Kanai, M
Du, W
Curran, DPcurran@pitt.eduCURRAN
Shibasaki, M
Date: 1 January 2003
Date Type: Publication
Journal or Publication Title: Heterocycles
Volume: 59
Number: 1
Page Range: 369 - 385
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0385-5414
Date Deposited: 06 Feb 2014 23:56
Last Modified: 29 Jan 2019 15:55
URI: http://d-scholarship.pitt.edu/id/eprint/20474

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