Diastereoisomeric atropisomers from the addition of lithiated N,N-dialkyl-l-naphthamides to aldehydes

Peter Bowles; Jonathan Clayden; Matthew Tomkinson

doi:10.1016/0040-4039(95)01945-E

Diastereoisomeric atropisomers from the addition of lithiated N,N-dialkyl-l-naphthamides to aldehydes

Peter Bowles^*, Jonathan Clayden, Matthew Tomkinson

^*Corresponding author for this work

School of Chemistry

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

48 Citations (Scopus)

Abstract

2-Substituted N,N-diethyl or N,N-diisopropyl 1-naphthamides exist as stable atropisomers. When the 2-substituent is a 1-hydroxyalkyl group, the atropisomers are separable diastereoisomers. Synthesis of these compounds by the addition of aldehydes to orholithiated N,N-dialkyl 1-naphthamides proceeds with moderate to good diastereoselectivity in favour of the aR*S* (syn) diastereoisomer.

Original language	English
Pages (from-to)	9219-9222
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	50
DOIs	https://doi.org/10.1016/0040-4039(95)01945-E
Publication status	Published - 11 Dec 1995

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Organic & Biological

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title = "Diastereoisomeric atropisomers from the addition of lithiated N,N-dialkyl-l-naphthamides to aldehydes",

abstract = "2-Substituted N,N-diethyl or N,N-diisopropyl 1-naphthamides exist as stable atropisomers. When the 2-substituent is a 1-hydroxyalkyl group, the atropisomers are separable diastereoisomers. Synthesis of these compounds by the addition of aldehydes to orholithiated N,N-dialkyl 1-naphthamides proceeds with moderate to good diastereoselectivity in favour of the aR*S* (syn) diastereoisomer.",

author = "Peter Bowles and Jonathan Clayden and Matthew Tomkinson",

year = "1995",

month = dec,

day = "11",

doi = "10.1016/0040-4039(95)01945-E",

language = "English",

volume = "36",

pages = "9219--9222",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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number = "50",

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TY - JOUR

T1 - Diastereoisomeric atropisomers from the addition of lithiated N,N-dialkyl-l-naphthamides to aldehydes

AU - Bowles, Peter

AU - Clayden, Jonathan

AU - Tomkinson, Matthew

PY - 1995/12/11

Y1 - 1995/12/11

N2 - 2-Substituted N,N-diethyl or N,N-diisopropyl 1-naphthamides exist as stable atropisomers. When the 2-substituent is a 1-hydroxyalkyl group, the atropisomers are separable diastereoisomers. Synthesis of these compounds by the addition of aldehydes to orholithiated N,N-dialkyl 1-naphthamides proceeds with moderate to good diastereoselectivity in favour of the aR*S* (syn) diastereoisomer.

AB - 2-Substituted N,N-diethyl or N,N-diisopropyl 1-naphthamides exist as stable atropisomers. When the 2-substituent is a 1-hydroxyalkyl group, the atropisomers are separable diastereoisomers. Synthesis of these compounds by the addition of aldehydes to orholithiated N,N-dialkyl 1-naphthamides proceeds with moderate to good diastereoselectivity in favour of the aR*S* (syn) diastereoisomer.

UR - https://www.scopus.com/pages/publications/0028793162

U2 - 10.1016/0040-4039(95)01945-E

DO - 10.1016/0040-4039(95)01945-E

M3 - Article (Academic Journal)

AN - SCOPUS:0028793162

SN - 0040-4039

VL - 36

SP - 9219

EP - 9222

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Diastereoisomeric atropisomers from the addition of lithiated N,N-dialkyl-l-naphthamides to aldehydes

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