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Synthesis 2010(13): 2254-2270  
DOI: 10.1055/s-0029-1218813
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Multidimensional Screening and Methodology Development for Condensations Involving Complex 1,2-Diketones

John R. Goodell, Bo Leng, Tracy K. Snyder, Aaron B. Beeler*, John A. Porco Jr.*
Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA
Fax: +1(617)3582847; e-Mail: porco@bu.edu;
Further Information

Publication History

Received 22 April 2010
Publication Date:
11 June 2010 (online)

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Abstract

Multidimensional reaction screening with complex cycloheptane-1,2-diones is described. The studies resulted in the discovery of regioselective Lewis acid mediated condensation reactions with substituted ureas, and a diastereoselective hydrogenation process that proceeds through an interesting isomerization of allylpalladium hydride.

Key words

reaction discovery - regioselectivity - condensation - diastereoselectivity­ - hydrogenations

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16

Crystallographic data for compound 9a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 771959. Copies can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].

17

See the supporting information for representative characterization data for compounds 22a, 22b, 23a, 41a, 41b, and 48, and X-ray crystal structure data for compound 9a. This information is available through the Internet at www.thieme-connect.com/ejournals/toc/synthesis.

21

Conformational analysis (Macromodel 9.6) using OPLS 2005 force field, optimization (JAGUAR 7.5, 1998 ed.) and B3LYP, 6-31g**, Schrodinger, Inc.: Portland, OR, 2008.