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

Ciril Jimeno; Ramon Rios; Patrick J. Carroll; Patrick J. Walsh

doi:10.1016/j.tet.2003.12.071

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

Ciril Jimeno, Ramon Rios, Patrick J. Carroll, Patrick J. Walsh

Chemistry

University of Pennsylvania

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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.

Original language	British English
Pages (from-to)	4543-4548
Number of pages	6
Journal	Tetrahedron
Volume	60
Issue number	20
DOIs	https://doi.org/10.1016/j.tet.2003.12.071
State	Published - 10 May 2004

Keywords

1,2-Addition reactions
Atropisomeric amides
Dialkylzinc reagents
Stereochemistry

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10.1016/j.tet.2003.12.071

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

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.",

keywords = "1,2-Addition reactions, Atropisomeric amides, Dialkylzinc reagents, Stereochemistry",

author = "Ciril Jimeno and Ramon Rios and Carroll, {Patrick J.} and Walsh, {Patrick J.}",

note = "Funding Information: We thank the Petroleum Research Fund (ACS-PRF 38021), administered by the American Chemical Society, and the University of Pennsylvania for support of this work. ",

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T1 - Rapid, highly diastereoselective addition of dialkylzinc reagents to atropisomeric 2-formyl arylamides

AU - Jimeno, Ciril

AU - Rios, Ramon

AU - Carroll, Patrick J.

AU - Walsh, Patrick J.

N1 - Funding Information: We thank the Petroleum Research Fund (ACS-PRF 38021), administered by the American Chemical Society, and the University of Pennsylvania for support of this work.

PY - 2004/5/10

Y1 - 2004/5/10

N2 - 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.

AB - 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.

KW - 1,2-Addition reactions

KW - Atropisomeric amides

KW - Dialkylzinc reagents

KW - Stereochemistry

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DO - 10.1016/j.tet.2003.12.071

M3 - Article

AN - SCOPUS:1942532912

SN - 0040-4020

VL - 60

SP - 4543

EP - 4548

JO - Tetrahedron

JF - Tetrahedron

IS - 20

ER -

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

Abstract

Keywords

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