[(BINAP)Re(O)Cl-3] as an efficient catalyst for olefination of chiral alpha-substituted aliphatic aldehydes
(2010) In Journal of Organometallic Chemistry 695(19-20). p.2220-2224- Abstract
- A convenient one-pot preparation of [(BINAP) Re(O)Cl-3] (6) is described. This complex was demonstrated to be an efficient catalyst for the olefination of aldehydes by reaction with alpha-diazo esters, with essentially quantitative yields and up to 98:2 geometric selectivity. The potential for using enantiopure [(BINAP)Re(O)Cl-3] (6) to promote an asymmetric kinetic resolution of racemic alpha-stereogenic aldehydes was investigated, but no enantiotopic discrimination was observed. Control experiments indicate that this lack of selectivity stems from the in-situ formation of a phosphonium ylide, which accounts for product formation in a non-metal associated reaction pathway. (C) 2010 Elsevier B. V. All rights reserved.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/1675437
- author
- Strand, Daniel LU and Rein, Tobias
- organization
- publishing date
- 2010
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Rhenium, Alkenes, Homogenous catalysis, Wittig reactions
- in
- Journal of Organometallic Chemistry
- volume
- 695
- issue
- 19-20
- pages
- 2220 - 2224
- publisher
- Elsevier
- external identifiers
-
- wos:000280847000009
- scopus:77955710542
- ISSN
- 0022-328X
- DOI
- 10.1016/j.jorganchem.2010.06.008
- 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
- e7c39cd9-6272-4d66-b5ab-c801beea1a07 (old id 1675437)
- date added to LUP
- 2016-04-01 14:47:37
- date last changed
- 2022-01-28 02:31:23
@article{e7c39cd9-6272-4d66-b5ab-c801beea1a07, abstract = {{A convenient one-pot preparation of [(BINAP) Re(O)Cl-3] (6) is described. This complex was demonstrated to be an efficient catalyst for the olefination of aldehydes by reaction with alpha-diazo esters, with essentially quantitative yields and up to 98:2 geometric selectivity. The potential for using enantiopure [(BINAP)Re(O)Cl-3] (6) to promote an asymmetric kinetic resolution of racemic alpha-stereogenic aldehydes was investigated, but no enantiotopic discrimination was observed. Control experiments indicate that this lack of selectivity stems from the in-situ formation of a phosphonium ylide, which accounts for product formation in a non-metal associated reaction pathway. (C) 2010 Elsevier B. V. All rights reserved.}}, author = {{Strand, Daniel and Rein, Tobias}}, issn = {{0022-328X}}, keywords = {{Rhenium; Alkenes; Homogenous catalysis; Wittig reactions}}, language = {{eng}}, number = {{19-20}}, pages = {{2220--2224}}, publisher = {{Elsevier}}, series = {{Journal of Organometallic Chemistry}}, title = {{[(BINAP)Re(O)Cl-3] as an efficient catalyst for olefination of chiral alpha-substituted aliphatic aldehydes}}, url = {{http://dx.doi.org/10.1016/j.jorganchem.2010.06.008}}, doi = {{10.1016/j.jorganchem.2010.06.008}}, volume = {{695}}, year = {{2010}}, }