Stereoarrays with an all-carbon quaternary center: diastereoselective desymmetrization of prochiral malonaldehydes


Linclau, Bruno, Cini, Elena, Oakes, Catherine S., Josse, Solen, Light, Mark and Ironmonger, Victoria (2012) Stereoarrays with an all-carbon quaternary center: diastereoselective desymmetrization of prochiral malonaldehydes. Angewandte Chemie International Edition, 51, (5), 1232-1235. (doi:10.1002/anie.201107370).

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Description/Abstract

Tamed by chelation: The MgBr2 chelation of prochiral malonaldehydes allows diastereoselective monoaddition reactions with allyl stannane nucleophiles (see scheme; PG=protecting group, TBDMS=tert-butyldiphenylmethylsilyl, Tr=trityl). In the same pot, addition of a second nucleophile proceeds in high diastereoselectivity to generate nonsymmetric products with up to five contiguous stereogenic centers, including a chiral all-carbon quaternary center.

Item Type: Article
ISSNs: 1433-7851 (print)
1521-3773 (electronic)
Related URLs:
Keywords: chelates, magnesium, nucleophilic addition, stereoselectivity, synthetic methods
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Natural and Environmental Sciences > Chemistry
ePrint ID: 209155
Date Deposited: 26 Jan 2012 13:34
Last Modified: 27 Mar 2014 19:50
URI: http://eprints.soton.ac.uk/id/eprint/209155

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