Lithium Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3-Sulfanyl-Oxetanes as Bioisosteres
File(s)Croft_et_al-2018-Chemistry_-_A_European_Journal.pdf (999.6 KB)
Published version
Author(s)
Croft, RA
Mousseau, JJ
Choi, C
Bull, JA
Type
Journal Article
Abstract
3-Sulfanyl-oxetanes are presented as promising novel bioisosteric replacements for thioesters or benzyl sulfides. From oxetan-3-ols, a mild and inexpensive Li catalyst enables chemoselective C–OH activation and thiol alkylation. Oxetane sulfides are formed from various thiols providing novel motifs in new chemical space and specifically as bioisosteres for thioesters due to their similar shape and electronic properties. Under the same conditions, various -activated secondary and tertiary alcohols are also successful. Derivatization of the oxetane sulfide linker provides further novel oxetane classes and building blocks. Comparisons of key physicochemical properties of the oxetane compounds to selected carbonyl and methylene analogues indicate that these motifs are suitable for incorporation into drug discovery efforts.
Date Issued
2017-12-20
Date Acceptance
2017-11-24
ISSN
0947-6539
Publisher
Wiley
Start Page
818
End Page
821
Journal / Book Title
Chemistry - A European Journal
Volume
24
Issue
4
Copyright Statement
© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Sponsor
Engineering & Physical Science Research Council (EPSRC)
Engineering & Physical Science Research Council (E
The Royal Society
The Royal Society
Grant Number
EP/J001538/1
EP/K503733/1
UF140161
RG150444
Subjects
bioisosteres
homogeneous catalysis
oxetanes
oxygen heterocycles
sulfides
03 Chemical Sciences
General Chemistry
Publication Status
Published