Atropisomeric benzamides and naphthamides as chiral auxiliaries

Jonathan Clayden; Madeleine Helliwell; Catherine McCarthy; Neil Westlund

doi:10.1039/b004682p

Atropisomeric benzamides and naphthamides as chiral auxiliaries

Jonathan Clayden, Madeleine Helliwell^*, Catherine McCarthy, Neil Westlund

^*Corresponding author for this work

School of Chemistry

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

42 Citations (Scopus)

Abstract

Atropisomeric compounds whose chirality resides in a rotationally restricted aryl-CONR₂ bond may be employed as chiral auxiliaries. The electron-withdrawing amide group causes problems in the diastereoselective functionalisation of enolates derived from atropisomeric phenyl esters, but a strategy based on atroposelective nucleophilic addition to a chiral aldehyde followed by stereospecific [3,3] sigmatropic rearrangement allows atropisomeric naphthamides to be used as auxiliaries. The auxiliaries are resolved by dynamic resolution during aminal formation using a proline-derived diamine.

Original language	English
Pages (from-to)	3232-3249
Number of pages	18
Journal	Perkin 1
Issue number	19
DOIs	https://doi.org/10.1039/b004682p
Publication status	Published - 14 Sept 2000

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title = "Atropisomeric benzamides and naphthamides as chiral auxiliaries",

abstract = "Atropisomeric compounds whose chirality resides in a rotationally restricted aryl-CONR2 bond may be employed as chiral auxiliaries. The electron-withdrawing amide group causes problems in the diastereoselective functionalisation of enolates derived from atropisomeric phenyl esters, but a strategy based on atroposelective nucleophilic addition to a chiral aldehyde followed by stereospecific [3,3] sigmatropic rearrangement allows atropisomeric naphthamides to be used as auxiliaries. The auxiliaries are resolved by dynamic resolution during aminal formation using a proline-derived diamine.",

author = "Jonathan Clayden and Madeleine Helliwell and Catherine McCarthy and Neil Westlund",

year = "2000",

month = sep,

day = "14",

doi = "10.1039/b004682p",

language = "English",

pages = "3232--3249",

journal = "Perkin 1",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Atropisomeric benzamides and naphthamides as chiral auxiliaries

AU - Clayden, Jonathan

AU - Helliwell, Madeleine

AU - McCarthy, Catherine

AU - Westlund, Neil

PY - 2000/9/14

Y1 - 2000/9/14

N2 - Atropisomeric compounds whose chirality resides in a rotationally restricted aryl-CONR2 bond may be employed as chiral auxiliaries. The electron-withdrawing amide group causes problems in the diastereoselective functionalisation of enolates derived from atropisomeric phenyl esters, but a strategy based on atroposelective nucleophilic addition to a chiral aldehyde followed by stereospecific [3,3] sigmatropic rearrangement allows atropisomeric naphthamides to be used as auxiliaries. The auxiliaries are resolved by dynamic resolution during aminal formation using a proline-derived diamine.

AB - Atropisomeric compounds whose chirality resides in a rotationally restricted aryl-CONR2 bond may be employed as chiral auxiliaries. The electron-withdrawing amide group causes problems in the diastereoselective functionalisation of enolates derived from atropisomeric phenyl esters, but a strategy based on atroposelective nucleophilic addition to a chiral aldehyde followed by stereospecific [3,3] sigmatropic rearrangement allows atropisomeric naphthamides to be used as auxiliaries. The auxiliaries are resolved by dynamic resolution during aminal formation using a proline-derived diamine.

UR - https://www.scopus.com/pages/publications/0034619274

U2 - 10.1039/b004682p

DO - 10.1039/b004682p

M3 - Article (Academic Journal)

AN - SCOPUS:0034619274

SN - 1470-4358

SP - 3232

EP - 3249

JO - Perkin 1

JF - Perkin 1

IS - 19

ER -

Atropisomeric benzamides and naphthamides as chiral auxiliaries

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