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

Record type: Article

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.

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Citation

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), pp. 1232-1235. (doi:10.1002/anie.201107370).

More information

e-pub ahead of print date: 23 December 2011
Published date: 27 January 2012
Keywords: chelates, magnesium, nucleophilic addition, stereoselectivity, synthetic methods
Organisations: Chemistry

Identifiers

Local EPrints ID: 209155
URI: http://eprints.soton.ac.uk/id/eprint/209155
ISSN: 1433-7851
PURE UUID: 7bfb1a6c-ea14-44e5-b3af-6ba5df62b34d
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 26 Jan 2012 13:34
Last modified: 18 Jul 2017 10:47

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Contributors

Author: Bruno Linclau ORCID iD
Author: Elena Cini
Author: Catherine S. Oakes
Author: Solen Josse
Author: Mark Light ORCID iD
Author: Victoria Ironmonger

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