New approach to biomimetic transamination using bifunctional [1,3]-proton transfer catalysis in thioxanthenyl dioxide imines.
(2002) In Journal of Organic Chemistry 67(11). p.3585-3594- Abstract
- A pyridoxamine equivalent, 9-aminothioxanthene 10,10-dioxide, has been designed that is capable of affording transamination in good to excellent yields of natural as well as artificial amino acids. Amidines and guanidines in catalytic amounts were capable of performing [1,3]-proton transfer in the imines under mild conditions, whereas various simple amines failed. The use of chiral catalysts resulted in modest asymmetric induction (ee </= 45%). The electronic dependence in para-substituted phenyl glyoxylate imines, isotope effects, and computational studies support a stepwise, bifunctional mechanism for amidine and guanidine catalysts. Attempts toward an autocatalytic model system are described.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/108500
- author
- Hjelmencrantz, Anders and Berg, Ulf LU
- organization
- publishing date
- 2002
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Journal of Organic Chemistry
- volume
- 67
- issue
- 11
- pages
- 3585 - 3594
- publisher
- The American Chemical Society (ACS)
- external identifiers
-
- pmid:12027668
- wos:000175915000006
- scopus:0037204686
- ISSN
- 1520-6904
- DOI
- 10.1021/jo0106748
- 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
- a0c74ef9-717e-4841-9502-e83ee6b20daa (old id 108500)
- date added to LUP
- 2016-04-01 12:30:14
- date last changed
- 2022-01-27 05:59:46
@article{a0c74ef9-717e-4841-9502-e83ee6b20daa, abstract = {{A pyridoxamine equivalent, 9-aminothioxanthene 10,10-dioxide, has been designed that is capable of affording transamination in good to excellent yields of natural as well as artificial amino acids. Amidines and guanidines in catalytic amounts were capable of performing [1,3]-proton transfer in the imines under mild conditions, whereas various simple amines failed. The use of chiral catalysts resulted in modest asymmetric induction (ee </= 45%). The electronic dependence in para-substituted phenyl glyoxylate imines, isotope effects, and computational studies support a stepwise, bifunctional mechanism for amidine and guanidine catalysts. Attempts toward an autocatalytic model system are described.}}, author = {{Hjelmencrantz, Anders and Berg, Ulf}}, issn = {{1520-6904}}, language = {{eng}}, number = {{11}}, pages = {{3585--3594}}, publisher = {{The American Chemical Society (ACS)}}, series = {{Journal of Organic Chemistry}}, title = {{New approach to biomimetic transamination using bifunctional [1,3]-proton transfer catalysis in thioxanthenyl dioxide imines.}}, url = {{http://dx.doi.org/10.1021/jo0106748}}, doi = {{10.1021/jo0106748}}, volume = {{67}}, year = {{2002}}, }