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Bicyclo[2.2.2]octane-derived chiral ligands-synthesis and application of BODOLs in the asymmetric reduction of acetophenone with catecholborane

Friberg, Annika LU ; Sarvary, Ian ; Wendt, Ola LU and Frejd, Torbjörn LU (2008) In Tetrahedron: Asymmetry 19(15). p.1765-1777
Abstract
An improved synthetic route to the bicyclo[2.2.2]octane-2,6-diol ligands (2,6-BODOLS) allowed an increased structural variation of the ligand side-arm. The addition of aromatic or vinylic Grignard reagents to hydroxyketone 1 was highly selective and ligands 3f-3I were isolated in 84-97% yield. The addition of alkyl Grignard reagents containing beta-hydrogens resulted in lower yields (13-71%) due to competing ketone reduction. A number of 2,5-BODOLs were synthesized using a similar methodology. The ligands, together with Ti(OiPr)(4), were tested in the asymmetric reduction of acetophenone with catecholborane (up to 98% ee). 1-Naphthyl-BODOL 3i was employed as an allylboration reagent to benzaldehyde together with Sc(OTf)(3), resulting in... (More)
An improved synthetic route to the bicyclo[2.2.2]octane-2,6-diol ligands (2,6-BODOLS) allowed an increased structural variation of the ligand side-arm. The addition of aromatic or vinylic Grignard reagents to hydroxyketone 1 was highly selective and ligands 3f-3I were isolated in 84-97% yield. The addition of alkyl Grignard reagents containing beta-hydrogens resulted in lower yields (13-71%) due to competing ketone reduction. A number of 2,5-BODOLs were synthesized using a similar methodology. The ligands, together with Ti(OiPr)(4), were tested in the asymmetric reduction of acetophenone with catecholborane (up to 98% ee). 1-Naphthyl-BODOL 3i was employed as an allylboration reagent to benzaldehyde together with Sc(OTf)(3), resulting in (1S)-1-phenyl-3-buten-1-ol in 80% ee. (C) 2008 Elsevier Ltd. All rights reserved. (Less)
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron: Asymmetry
volume
19
issue
15
pages
1765 - 1777
publisher
Elsevier
external identifiers
  • wos:000259623600002
  • scopus:49049087875
ISSN
0957-4166
DOI
10.1016/j.tetasy.2008.07.006
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
id
cc3538e0-80d0-43e4-b004-7340f45b96aa (old id 1286922)
date added to LUP
2016-04-01 13:01:19
date last changed
2022-01-27 08:51:39
@article{cc3538e0-80d0-43e4-b004-7340f45b96aa,
  abstract     = {{An improved synthetic route to the bicyclo[2.2.2]octane-2,6-diol ligands (2,6-BODOLS) allowed an increased structural variation of the ligand side-arm. The addition of aromatic or vinylic Grignard reagents to hydroxyketone 1 was highly selective and ligands 3f-3I were isolated in 84-97% yield. The addition of alkyl Grignard reagents containing beta-hydrogens resulted in lower yields (13-71%) due to competing ketone reduction. A number of 2,5-BODOLs were synthesized using a similar methodology. The ligands, together with Ti(OiPr)(4), were tested in the asymmetric reduction of acetophenone with catecholborane (up to 98% ee). 1-Naphthyl-BODOL 3i was employed as an allylboration reagent to benzaldehyde together with Sc(OTf)(3), resulting in (1S)-1-phenyl-3-buten-1-ol in 80% ee. (C) 2008 Elsevier Ltd. All rights reserved.}},
  author       = {{Friberg, Annika and Sarvary, Ian and Wendt, Ola and Frejd, Torbjörn}},
  issn         = {{0957-4166}},
  language     = {{eng}},
  number       = {{15}},
  pages        = {{1765--1777}},
  publisher    = {{Elsevier}},
  series       = {{Tetrahedron: Asymmetry}},
  title        = {{Bicyclo[2.2.2]octane-derived chiral ligands-synthesis and application of BODOLs in the asymmetric reduction of acetophenone with catecholborane}},
  url          = {{http://dx.doi.org/10.1016/j.tetasy.2008.07.006}},
  doi          = {{10.1016/j.tetasy.2008.07.006}},
  volume       = {{19}},
  year         = {{2008}},
}