Synthesis of atropisomeric diamides with remotely related stereogenic axes by stereoselective additions to imines

Jonathan Clayden; Neil Westlund; Francis X. Wilson

doi:10.1016/S0040-4039(99)00520-1

Synthesis of atropisomeric diamides with remotely related stereogenic axes by stereoselective additions to imines

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

27 Citations (Scopus)

Abstract

Atroposelective addition of axially chiral laterally lithiated 2-alkyl- 1-naphthamides to 6-substituted 2-(N-methylformimino)benzamides leads, after equilibration of the new stereogenic axis to its more stable conformation, to single atropisomeric diastereoisomers of diamides bearing remotely related stereogenic axes separated by one or two stereogenic centres. The newly created MeNH-bearing stereogenic centre 'relays' stereochemical information from the first axis to the second.

Original language	English
Pages (from-to)	3331-3334
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4039(99)00520-1
Publication status	Published - 23 Apr 1999

Access to Document

10.1016/S0040-4039(99)00520-1

Handle.net

Persistent link

Cite this

@article{993176de0132419d9a0ddbef94febb4e,

title = "Synthesis of atropisomeric diamides with remotely related stereogenic axes by stereoselective additions to imines",

abstract = "Atroposelective addition of axially chiral laterally lithiated 2-alkyl- 1-naphthamides to 6-substituted 2-(N-methylformimino)benzamides leads, after equilibration of the new stereogenic axis to its more stable conformation, to single atropisomeric diastereoisomers of diamides bearing remotely related stereogenic axes separated by one or two stereogenic centres. The newly created MeNH-bearing stereogenic centre 'relays' stereochemical information from the first axis to the second.",

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

year = "1999",

month = apr,

day = "23",

doi = "10.1016/S0040-4039(99)00520-1",

language = "English",

volume = "40",

pages = "3331--3334",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "17",

}

TY - JOUR

T1 - Synthesis of atropisomeric diamides with remotely related stereogenic axes by stereoselective additions to imines

AU - Clayden, Jonathan

AU - Westlund, Neil

AU - Wilson, Francis X.

PY - 1999/4/23

Y1 - 1999/4/23

N2 - Atroposelective addition of axially chiral laterally lithiated 2-alkyl- 1-naphthamides to 6-substituted 2-(N-methylformimino)benzamides leads, after equilibration of the new stereogenic axis to its more stable conformation, to single atropisomeric diastereoisomers of diamides bearing remotely related stereogenic axes separated by one or two stereogenic centres. The newly created MeNH-bearing stereogenic centre 'relays' stereochemical information from the first axis to the second.

AB - Atroposelective addition of axially chiral laterally lithiated 2-alkyl- 1-naphthamides to 6-substituted 2-(N-methylformimino)benzamides leads, after equilibration of the new stereogenic axis to its more stable conformation, to single atropisomeric diastereoisomers of diamides bearing remotely related stereogenic axes separated by one or two stereogenic centres. The newly created MeNH-bearing stereogenic centre 'relays' stereochemical information from the first axis to the second.

UR - http://www.scopus.com/inward/record.url?scp=0033597159&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)00520-1

DO - 10.1016/S0040-4039(99)00520-1

M3 - Article (Academic Journal)

AN - SCOPUS:0033597159

SN - 0040-4039

VL - 40

SP - 3331

EP - 3334

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

Synthesis of atropisomeric diamides with remotely related stereogenic axes by stereoselective additions to imines

Abstract

Access to Document

Handle.net

Other files and links

Fingerprint

Cite this