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Expanding the scope of methyl xanthate esters - From Barton-McCombie reaction auxiliary to versatile protective group

Thorsheim, Karin LU ; Manner, Sophie LU and Ellervik, Ulf LU (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.

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author
organization
publishing date
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
2018-01-16 13:22:11
@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},
  keyword      = {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},
  volume       = {73},
  year         = {2017},
}