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...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2015
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| Online Access: | https://hdl.handle.net/10356/103844 http://hdl.handle.net/10220/24638 |
| _version_ | 1811697553698193408 |
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| author | Zong, Lili Ban, Xu Kee, Choon Wee Tan, Choon-Hong |
| 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 |
| author_sort | Zong, Lili |
| collection | NTU |
| 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. |
| first_indexed | 2024-10-01T07:57:06Z |
| format | Journal Article |
| id | ntu-10356/103844 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:57:06Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-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. |
| 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 |
| title | 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_short | 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 |
| topic | DRNTU::Science::Chemistry::Physical chemistry::Catalysis |
| url | https://hdl.handle.net/10356/103844 http://hdl.handle.net/10220/24638 |
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