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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 (2018) In Chemistry - A European Journal 24(10). p.2344-2348
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.

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author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Asymmetric catalysis, Cyclooctatetraenes, Fenestrenes, Planar chirality, Rhodium
in
Chemistry - A European Journal
volume
24
issue
10
pages
2344 - 2348
publisher
Wiley-Blackwell
external identifiers
  • pmid:29131428
  • 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
2024-09-16 13:47:49
@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}},
  keywords     = {{Asymmetric catalysis; Cyclooctatetraenes; Fenestrenes; Planar chirality; Rhodium}},
  language     = {{eng}},
  month        = {{02}},
  number       = {{10}},
  pages        = {{2344--2348}},
  publisher    = {{Wiley-Blackwell}},
  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}},
  doi          = {{10.1002/chem.201704816}},
  volume       = {{24}},
  year         = {{2018}},
}