Catalytic enantioselective alkylation of sulfenate anions to chiral heterocyclic sulfoxides using halogenated pentanidium salts

Catalytic enantioselective alkylation of sulfenate anions to chiral heterocyclic sulfoxides using halogenated pentanidium salts

We report halogenated pentanidiums as phase-transfer catalysts for the asymmetric alkylation of sulfenate anions to various sulfoxides with high enantioselectivities (up to 99 % ee) and yields (up to 99 %). This approach gives access to enantioenriched heterocyclic sulfoxides that might not be compa...

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Main Authors: Zong, Lili, Ban, Xu, Kee, Choon Wee, Tan, Choon-Hong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2015
Subjects:
DRNTU::Science::Chemistry::Physical chemistry::Catalysis
Online Access:https://hdl.handle.net/10356/103844
http://hdl.handle.net/10220/24638
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1038442020-03-07T12:34:40Z Catalytic enantioselective alkylation of sulfenate anions to chiral heterocyclic sulfoxides using halogenated pentanidium salts Zong, Lili Ban, Xu Kee, Choon Wee Tan, Choon-Hong School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Physical chemistry::Catalysis We report halogenated pentanidiums as phase-transfer catalysts for the asymmetric alkylation of sulfenate anions to various sulfoxides with high enantioselectivities (up to 99 % ee) and yields (up to 99 %). This approach gives access to enantioenriched heterocyclic sulfoxides that might not be compatible with strong oxidants or organometallic reagents. Computational studies have revealed that the multiple noncovalent interactions such as halogen bonds and nonclassical hydrogen bonds are involved. 2015-01-15T08:16:41Z 2019-12-06T21:21:28Z 2015-01-15T08:16:41Z 2019-12-06T21:21:28Z 2014 2014 Journal Article g, L., Ban, X., Kee, C. W., & Tan, C.-H. (2014). Catalytic enantioselective alkylation of sulfenate anions to chiral heterocyclic sulfoxides using halogenated pentanidium salts. Angewandte chemie international edition, 53(44), 11849-11853. 1433-7851 https://hdl.handle.net/10356/103844 http://hdl.handle.net/10220/24638 10.1002/anie.201407512 en Angewandte chemie international edition © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Physical chemistry::Catalysis
spellingShingle DRNTU::Science::Chemistry::Physical chemistry::Catalysis
Zong, Lili
Ban, Xu
Kee, Choon Wee
Tan, Choon-Hong
Catalytic enantioselective alkylation of sulfenate anions to chiral heterocyclic sulfoxides using halogenated pentanidium salts
description We report halogenated pentanidiums as phase-transfer catalysts for the asymmetric alkylation of sulfenate anions to various sulfoxides with high enantioselectivities (up to 99 % ee) and yields (up to 99 %). This approach gives access to enantioenriched heterocyclic sulfoxides that might not be compatible with strong oxidants or organometallic reagents. Computational studies have revealed that the multiple noncovalent interactions such as halogen bonds and nonclassical hydrogen bonds are involved.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Zong, Lili
Ban, Xu
Kee, Choon Wee
Tan, Choon-Hong
format Article
author Zong, Lili
Ban, Xu
Kee, Choon Wee
Tan, Choon-Hong
author_sort Zong, Lili
title Catalytic enantioselective alkylation of sulfenate anions to chiral heterocyclic sulfoxides using halogenated pentanidium salts
title_short Catalytic enantioselective alkylation of sulfenate anions to chiral heterocyclic sulfoxides using halogenated pentanidium salts
title_full Catalytic enantioselective alkylation of sulfenate anions to chiral heterocyclic sulfoxides using halogenated pentanidium salts
title_fullStr Catalytic enantioselective alkylation of sulfenate anions to chiral heterocyclic sulfoxides using halogenated pentanidium salts
title_full_unstemmed Catalytic enantioselective alkylation of sulfenate anions to chiral heterocyclic sulfoxides using halogenated pentanidium salts
title_sort catalytic enantioselective alkylation of sulfenate anions to chiral heterocyclic sulfoxides using halogenated pentanidium salts
publishDate 2015
url https://hdl.handle.net/10356/103844
http://hdl.handle.net/10220/24638
_version_ 1681047542153871360

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