Expanding the scope of methyl xanthate esters - From Barton-McCombie reaction auxiliary to versatile protective group
(2017) In Tetrahedron 73(44). p.6329-6333- Abstract
The methyl xanthate ester is presented as a versatile protective group for alcohols. Hydroxyl groups can easily be transformed into methyl xanthate esters by several methods and are commonly used as an auxiliary in the Barton-McCombie reaction. We show that these methyl xanthate esters can readily and chemoselectively be cleaved under mild conditions by the action of diethylenetriamine using microwave heating. This method is orthogonal to many common hydroxyl protective groups that can be introduced and cleaved in the presence of methyl xanthate ester.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/65ec556f-d89a-4371-aad8-2b31d4461bf0
- author
- Thorsheim, Karin
LU
; Manner, Sophie
LU
and Ellervik, Ulf
LU
- organization
- publishing date
- 2017
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Alcohol protection, Chemoselective, Deprotection, Diethylenetriamine, Methyl xanthate ester
- in
- Tetrahedron
- volume
- 73
- issue
- 44
- pages
- 6329 - 6333
- publisher
- Elsevier
- external identifiers
-
- scopus:85029793868
- wos:000413798200010
- ISSN
- 0040-4020
- DOI
- 10.1016/j.tet.2017.09.022
- language
- English
- LU publication?
- yes
- id
- 65ec556f-d89a-4371-aad8-2b31d4461bf0
- date added to LUP
- 2017-10-10 07:28:01
- date last changed
- 2025-01-07 22:23:52
@article{65ec556f-d89a-4371-aad8-2b31d4461bf0, abstract = {{<p>The methyl xanthate ester is presented as a versatile protective group for alcohols. Hydroxyl groups can easily be transformed into methyl xanthate esters by several methods and are commonly used as an auxiliary in the Barton-McCombie reaction. We show that these methyl xanthate esters can readily and chemoselectively be cleaved under mild conditions by the action of diethylenetriamine using microwave heating. This method is orthogonal to many common hydroxyl protective groups that can be introduced and cleaved in the presence of methyl xanthate ester.</p>}}, author = {{Thorsheim, Karin and Manner, Sophie and Ellervik, Ulf}}, issn = {{0040-4020}}, keywords = {{Alcohol protection; Chemoselective; Deprotection; Diethylenetriamine; Methyl xanthate ester}}, language = {{eng}}, number = {{44}}, pages = {{6329--6333}}, publisher = {{Elsevier}}, series = {{Tetrahedron}}, title = {{Expanding the scope of methyl xanthate esters - From Barton-McCombie reaction auxiliary to versatile protective group}}, url = {{http://dx.doi.org/10.1016/j.tet.2017.09.022}}, doi = {{10.1016/j.tet.2017.09.022}}, volume = {{73}}, year = {{2017}}, }