Synthesis of atropisomeric 2-(1-aminoalkyl)-1-naphthamides by stereoselective addition of organolithiums to a 2-imino-1-naphthamide

Jonathan Clayden; Neil Westlund; Francis X. Wilson

doi:10.1016/S0040-4039(99)00519-5

Synthesis of atropisomeric 2-(1-aminoalkyl)-1-naphthamides by stereoselective addition of organolithiums to a 2-imino-1-naphthamide

Jonathan Clayden^*, Neil Westlund, Francis X. Wilson

^*Corresponding author for this work

School of Chemistry

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

22 Citations (Scopus)

Abstract

Unlike the corresponding aldehydes, 2-(N-methylformimino)-N,N-dialkyl- 1-naphthamides react highly atroposelectively with simple organolithium reagents to give atropisomeric amines whose syn stereochemistry is thermodynamically preferred over anti.

Original language	English
Pages (from-to)	3329-3330
Number of pages	2
Journal	Tetrahedron Letters
Volume	40
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4039(99)00519-5
Publication status	Published - 23 Apr 1999

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Organic & Biological

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@article{94ceff975b5f4e4a94800b5821c82f79,

title = "Synthesis of atropisomeric 2-(1-aminoalkyl)-1-naphthamides by stereoselective addition of organolithiums to a 2-imino-1-naphthamide",

abstract = "Unlike the corresponding aldehydes, 2-(N-methylformimino)-N,N-dialkyl- 1-naphthamides react highly atroposelectively with simple organolithium reagents to give atropisomeric amines whose syn stereochemistry is thermodynamically preferred over anti.",

author = "Jonathan Clayden and Neil Westlund and Wilson, \{Francis X.\}",

year = "1999",

month = apr,

day = "23",

doi = "10.1016/S0040-4039(99)00519-5",

language = "English",

volume = "40",

pages = "3329--3330",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "17",

}

TY - JOUR

T1 - Synthesis of atropisomeric 2-(1-aminoalkyl)-1-naphthamides by stereoselective addition of organolithiums to a 2-imino-1-naphthamide

AU - Clayden, Jonathan

AU - Westlund, Neil

AU - Wilson, Francis X.

PY - 1999/4/23

Y1 - 1999/4/23

N2 - Unlike the corresponding aldehydes, 2-(N-methylformimino)-N,N-dialkyl- 1-naphthamides react highly atroposelectively with simple organolithium reagents to give atropisomeric amines whose syn stereochemistry is thermodynamically preferred over anti.

AB - Unlike the corresponding aldehydes, 2-(N-methylformimino)-N,N-dialkyl- 1-naphthamides react highly atroposelectively with simple organolithium reagents to give atropisomeric amines whose syn stereochemistry is thermodynamically preferred over anti.

UR - https://www.scopus.com/pages/publications/0033597321

U2 - 10.1016/S0040-4039(99)00519-5

DO - 10.1016/S0040-4039(99)00519-5

M3 - Article (Academic Journal)

AN - SCOPUS:0033597321

SN - 0040-4039

VL - 40

SP - 3329

EP - 3330

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

Synthesis of atropisomeric 2-(1-aminoalkyl)-1-naphthamides by stereoselective addition of organolithiums to a 2-imino-1-naphthamide

Abstract

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