Remote stereocontrol using rotationally restricted amides: (1,5)-Asymmetric induction

Jonathan Clayden; Megan Darbyshire; Jennifer H. Pink; Neil Westlund; Francis X. Wilson

doi:10.1016/S0040-4039(97)10289-1

Remote stereocontrol using rotationally restricted amides: (1,5)-Asymmetric induction

Jonathan Clayden^*, Megan Darbyshire, Jennifer H. Pink, Neil Westlund, Francis X. Wilson

^*Corresponding author for this work

School of Chemistry

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

25 Citations (Scopus)

Abstract

The stereochemical influence of a rotationally restricted amide group extends widely across substituted aromatic amides. Stereogenic centres can be created with high levels of (1,5)-stereocontrol when electrophiles are added to the enolates of 2-ketonaphthamides or to lithiated 2-alkylnaphthamides. Sequential double lateral lithiation of 2,6-dialkylbenzamides can lead to compounds containing (1,5) related stereogenic centres by a process of two-directional asymmetric induction.

Original language	English
Pages (from-to)	8587-8590
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4039(97)10289-1
Publication status	Published - 8 Dec 1997

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abstract = "The stereochemical influence of a rotationally restricted amide group extends widely across substituted aromatic amides. Stereogenic centres can be created with high levels of (1,5)-stereocontrol when electrophiles are added to the enolates of 2-ketonaphthamides or to lithiated 2-alkylnaphthamides. Sequential double lateral lithiation of 2,6-dialkylbenzamides can lead to compounds containing (1,5) related stereogenic centres by a process of two-directional asymmetric induction.",

author = "Jonathan Clayden and Megan Darbyshire and Pink, {Jennifer H.} and Neil Westlund and Wilson, {Francis X.}",

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T1 - Remote stereocontrol using rotationally restricted amides

T2 - (1,5)-Asymmetric induction

AU - Clayden, Jonathan

AU - Darbyshire, Megan

AU - Pink, Jennifer H.

AU - Westlund, Neil

AU - Wilson, Francis X.

PY - 1997/12/8

Y1 - 1997/12/8

N2 - The stereochemical influence of a rotationally restricted amide group extends widely across substituted aromatic amides. Stereogenic centres can be created with high levels of (1,5)-stereocontrol when electrophiles are added to the enolates of 2-ketonaphthamides or to lithiated 2-alkylnaphthamides. Sequential double lateral lithiation of 2,6-dialkylbenzamides can lead to compounds containing (1,5) related stereogenic centres by a process of two-directional asymmetric induction.

AB - The stereochemical influence of a rotationally restricted amide group extends widely across substituted aromatic amides. Stereogenic centres can be created with high levels of (1,5)-stereocontrol when electrophiles are added to the enolates of 2-ketonaphthamides or to lithiated 2-alkylnaphthamides. Sequential double lateral lithiation of 2,6-dialkylbenzamides can lead to compounds containing (1,5) related stereogenic centres by a process of two-directional asymmetric induction.

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U2 - 10.1016/S0040-4039(97)10289-1

DO - 10.1016/S0040-4039(97)10289-1

M3 - Article (Academic Journal)

AN - SCOPUS:0030721030

SN - 0040-4039

VL - 38

SP - 8587

EP - 8590

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -

Remote stereocontrol using rotationally restricted amides: (1,5)-Asymmetric induction

Abstract

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