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Control of Enantioselectivity in Rhodium(I) Catalysis by Planar Chiral Dibenzo[a,e]cyclooctatetraenes

Melcher, Michaela Christina LU ; Ivšić, Trpimir LU ; Olagnon, Charlotte; Tenten, Christina; Lützen, Arne and Strand, Daniel LU (2017) In Chemistry - A European Journal
Abstract

Planar chiral 5,11-disubstiuted dibenzo[a,e]cyclo-octatetraenes (dbCOTs) have been developed as the first useful chiral homologs to dbCOT-ligands for asymmetric applications. Methods enabling the preparation of such compounds on a gram-scale in enantiomerically pure form are described. Evaluated as ligands in rhodium(I)-catalyzed 1,4- and 1,2-arylation reactions, tertiary and quarternary stereogenic centers were formed with excellent yields and selectivities of up to >99%ee. A catalytic asymmetric synthesis of a key cyclization precursor to (-)-penifulvinA highlights the system in an applied context.

Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
epub
subject
keywords
Asymmetric catalysis, Cyclooctatetraenes, Fenestrenes, Planar chirality, Rhodium
in
Chemistry - A European Journal
publisher
John Wiley & Sons
external identifiers
  • scopus:85038015094
ISSN
0947-6539
DOI
10.1002/chem.201704816
language
English
LU publication?
yes
id
81064f1a-0be6-4c23-a9f7-1405dc5e4bbc
date added to LUP
2018-01-05 07:20:37
date last changed
2018-01-06 03:00:09
@article{81064f1a-0be6-4c23-a9f7-1405dc5e4bbc,
  abstract     = {<p>Planar chiral 5,11-disubstiuted dibenzo[a,e]cyclo-octatetraenes (dbCOTs) have been developed as the first useful chiral homologs to dbCOT-ligands for asymmetric applications. Methods enabling the preparation of such compounds on a gram-scale in enantiomerically pure form are described. Evaluated as ligands in rhodium(I)-catalyzed 1,4- and 1,2-arylation reactions, tertiary and quarternary stereogenic centers were formed with excellent yields and selectivities of up to &gt;99%ee. A catalytic asymmetric synthesis of a key cyclization precursor to (-)-penifulvinA highlights the system in an applied context.</p>},
  author       = {Melcher, Michaela Christina and Ivšić, Trpimir and Olagnon, Charlotte and Tenten, Christina and Lützen, Arne and Strand, Daniel},
  issn         = {0947-6539},
  keyword      = {Asymmetric catalysis,Cyclooctatetraenes,Fenestrenes,Planar chirality,Rhodium},
  language     = {eng},
  month        = {12},
  publisher    = {John Wiley & Sons},
  series       = {Chemistry - A European Journal},
  title        = {Control of Enantioselectivity in Rhodium(I) Catalysis by Planar Chiral Dibenzo[a,e]cyclooctatetraenes},
  url          = {http://dx.doi.org/10.1002/chem.201704816},
  year         = {2017},
}