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Rapid, highly diastereoselective addition of dialkylzinc reagents to atropisomeric 2-formyl arylamides

Rapid, highly diastereoselective addition of dialkylzinc reagents to atropisomeric 2-formyl arylamides
Rapid, highly diastereoselective addition of dialkylzinc reagents to atropisomeric 2-formyl arylamides
We have observed that dialkylzinc reagents add to atropisomeric 2-formyl arylamides many times faster than they react with other substituted benzaldehyde derivatives. Additionally, with diethylzinc the products were formed with very high diastereoselectivity, affording the syn product (d.r. greater than 95:5), except in one case where epimerization of the product is rapid. In contrast, Grignard and trialkylaluminum reagents afforded the anti diastereomers, with diminished stereoselectivity and formation of reduction products.
dialkylzinc reagents, atropisomeric amides, stereochemistry, 1, 2-addition reactions
0040-4020
4543-4548
Jimeno, Ciril
bb1d9511-2ffe-4d30-8a43-07f24281ae63
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Carroll, Patrick J.
93d7f675-b825-4733-8149-52f270403214
Walsh, Patrick J.
f2965fbd-ae13-43f9-8f30-50d5aabe73fc
Jimeno, Ciril
bb1d9511-2ffe-4d30-8a43-07f24281ae63
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Carroll, Patrick J.
93d7f675-b825-4733-8149-52f270403214
Walsh, Patrick J.
f2965fbd-ae13-43f9-8f30-50d5aabe73fc

Jimeno, Ciril, Rios, Ramon, Carroll, Patrick J. and Walsh, Patrick J. (2004) Rapid, highly diastereoselective addition of dialkylzinc reagents to atropisomeric 2-formyl arylamides. Tetrahedron, 60 (20), 4543-4548. (doi:10.1016/j.tet.2003.12.071).

Record type: Article

Abstract

We have observed that dialkylzinc reagents add to atropisomeric 2-formyl arylamides many times faster than they react with other substituted benzaldehyde derivatives. Additionally, with diethylzinc the products were formed with very high diastereoselectivity, affording the syn product (d.r. greater than 95:5), except in one case where epimerization of the product is rapid. In contrast, Grignard and trialkylaluminum reagents afforded the anti diastereomers, with diminished stereoselectivity and formation of reduction products.

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More information

Published date: 10 May 2004
Keywords: dialkylzinc reagents, atropisomeric amides, stereochemistry, 1, 2-addition reactions
Organisations: Chemistry

Identifiers

Local EPrints ID: 347998
URI: http://eprints.soton.ac.uk/id/eprint/347998
ISSN: 0040-4020
PURE UUID: 829a1333-65bd-4126-8ffa-a08dbd2de990
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 05 Feb 2013 11:18
Last modified: 19 Nov 2019 01:38

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