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 |
| Item ID: | 209155 |
| Date Deposited: | 26 Jan 2012 13:34 |
| Last Modified: | 26 Apr 2013 01:26 |
| Contributors: | Linclau, Bruno (Author) Cini, Elena (Author) Oakes, Catherine S. (Author) Josse, Solen (Author) Light, Mark (Author) Ironmonger, Victoria (Author) |
| Date: | 27 January 2012 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/209155 |
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