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

Stereoarrays with an all-carbon quaternary center: diastereoselective desymmetrization of prochiral malonaldehydes
Stereoarrays with an all-carbon quaternary center: diastereoselective desymmetrization of prochiral malonaldehydes
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.
chelates, magnesium, nucleophilic addition, stereoselectivity, synthetic methods
1433-7851
1232-1235
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Cini, Elena
d6050a68-9691-4fe3-a499-99c1b63a9459
Oakes, Catherine S.
ef0c51fc-f7f1-4c90-bf8b-6c85da4af284
Josse, Solen
512a0636-acc9-41fa-a587-152bd8ca13b5
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Ironmonger, Victoria
40468cb0-b103-4c88-b817-18d43d1b811a
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Cini, Elena
d6050a68-9691-4fe3-a499-99c1b63a9459
Oakes, Catherine S.
ef0c51fc-f7f1-4c90-bf8b-6c85da4af284
Josse, Solen
512a0636-acc9-41fa-a587-152bd8ca13b5
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Ironmonger, Victoria
40468cb0-b103-4c88-b817-18d43d1b811a

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).

Record type: Article

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.

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More information

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

Identifiers

Local EPrints ID: 209155
URI: http://eprints.soton.ac.uk/id/eprint/209155
DOI: doi:10.1002/anie.201107370
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: 15 Mar 2024 03:05

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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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