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:	Creators Email Pitt Username ORCID Yabu, K Masumoto, S Kanai, M Du, W Curran, DP curran@pitt.edu CURRAN Shibasaki, M
Date:	1 January 2003
Date Type:	Publication
Journal or Publication Title:	Heterocycles
Volume:	59
Number:	1
Page Range:	369 - 385
DOI or Unique Handle:	10.3987/com-02-s49
Schools and Programs:	Dietrich School of Arts and Sciences > Chemistry
Refereed:	Yes
ISSN:	0385-5414
Date Deposited:	06 Feb 2014 23:56
Last Modified:	15 Aug 2020 12:55
URI:	http://d-scholarship-dev.library.pitt.edu/id/eprint/20474

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