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
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
10 May 2004
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), .
(doi:10.1016/j.tet.2003.12.071).
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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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
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Date deposited: 05 Feb 2013 11:18
Last modified: 14 Mar 2024 12:54
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Contributors
Author:
Ciril Jimeno
Author:
Patrick J. Carroll
Author:
Patrick J. Walsh
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