Atroposelectivity in the reactions of ortholithiated aromatic tertiary amides with aldehydes

Peter Bowles; Jonathan Clayden; Madeleine Helliwell; Catherine McCarthy; Matthew Tomkinson; Neil Westlund

doi:10.1039/A701671I

Atroposelectivity in the reactions of ortholithiated aromatic tertiary amides with aldehydes

Peter Bowles, Jonathan Clayden^*, Madeleine Helliwell, Catherine McCarthy, Matthew Tomkinson, Neil Westlund

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal)

81 Citations (Scopus)

Abstract

The products of the addition of ortholithiated N,N-dialkylnaphthamides to aldehydes are pairs of stable, diastereoisomeric atropisomers, formed with selectivities of up to 90:10 in favour of the syn-atropisomer.

Original language	English
Pages (from-to)	2607-2616
Number of pages	10
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	17
DOIs	https://doi.org/10.1039/A701671I
Publication status	Published - 7 Sep 1997

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Bowles, P., Clayden, J., Helliwell, M., McCarthy, C., Tomkinson, M., & Westlund, N. (1997). Atroposelectivity in the reactions of ortholithiated aromatic tertiary amides with aldehydes. Journal of the Chemical Society, Perkin Transactions 1, (17), 2607-2616. https://doi.org/10.1039/A701671I

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abstract = "The products of the addition of ortholithiated N,N-dialkylnaphthamides to aldehydes are pairs of stable, diastereoisomeric atropisomers, formed with selectivities of up to 90:10 in favour of the syn-atropisomer.",

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Atroposelectivity in the reactions of ortholithiated aromatic tertiary amides with aldehydes. / Bowles, Peter; Clayden, Jonathan; Helliwell, Madeleine; McCarthy, Catherine; Tomkinson, Matthew; Westlund, Neil.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 17, 07.09.1997, p. 2607-2616.

Research output: Contribution to journal › Article (Academic Journal)

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T1 - Atroposelectivity in the reactions of ortholithiated aromatic tertiary amides with aldehydes

AU - Bowles, Peter

AU - Clayden, Jonathan

AU - Helliwell, Madeleine

AU - McCarthy, Catherine

AU - Tomkinson, Matthew

AU - Westlund, Neil

PY - 1997/9/7

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AB - The products of the addition of ortholithiated N,N-dialkylnaphthamides to aldehydes are pairs of stable, diastereoisomeric atropisomers, formed with selectivities of up to 90:10 in favour of the syn-atropisomer.

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