Carbene-catalyzed desymmetrization of 1,3-diols: access to optically enriched tertiary alkyl chlorides
The introduction of a chlorine atom to a carbon center in an enantioselective manner via conventional C–Cl bond formation is difficult. Here we report a new approach to this class of tertiary alkyl chlorides with high optical purities. Instead of forming a new C–Cl bond, our approach involves carben...
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sg-ntu-dr.10356-822232023-02-28T19:35:31Z Carbene-catalyzed desymmetrization of 1,3-diols: access to optically enriched tertiary alkyl chlorides Li, Bao-Sheng Wang, Yuhuang Proctor, Rupert S. J. Jin, Zhichao Chi, Yonggui Robin School of Physical and Mathematical Sciences Tertiary alkyl chlorides Carbene-catalyzed reactions The introduction of a chlorine atom to a carbon center in an enantioselective manner via conventional C–Cl bond formation is difficult. Here we report a new approach to this class of tertiary alkyl chlorides with high optical purities. Instead of forming a new C–Cl bond, our approach involves carbene-catalyzed desymmetrization of 2-chloro-1,3-diols as the key step to set up the chiral carbon center with excellent enantiomeric excess. NRF (Natl Research Foundation, S’pore) MOE (Min. of Education, S’pore) Accepted version 2017-07-31T04:04:02Z 2019-12-06T14:51:10Z 2017-07-31T04:04:02Z 2019-12-06T14:51:10Z 2016 Journal Article Li, B.-S., Wang, Y., Proctor, R. S. J., Jin, Z., & Chi, Y. R. (2016). Carbene-catalyzed desymmetrization of 1,3-diols: access to optically enriched tertiary alkyl chlorides. Chemical Communications, 52(53), 8313-8316. 1359-7345 https://hdl.handle.net/10356/82223 http://hdl.handle.net/10220/43497 10.1039/C6CC03345H en Chemical Communications © 2016 The Royal Society of Chemistry. This is the author created version of a work that has been peer reviewed and accepted for publication by Chemical Communications, The Royal Society of Chemistry. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1039/C6CC03345H]. 4 p. application/pdf |
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Nanyang Technological University |
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Tertiary alkyl chlorides Carbene-catalyzed reactions |
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Tertiary alkyl chlorides Carbene-catalyzed reactions Li, Bao-Sheng Wang, Yuhuang Proctor, Rupert S. J. Jin, Zhichao Chi, Yonggui Robin Carbene-catalyzed desymmetrization of 1,3-diols: access to optically enriched tertiary alkyl chlorides |
| description |
The introduction of a chlorine atom to a carbon center in an enantioselective manner via conventional C–Cl bond formation is difficult. Here we report a new approach to this class of tertiary alkyl chlorides with high optical purities. Instead of forming a new C–Cl bond, our approach involves carbene-catalyzed desymmetrization of 2-chloro-1,3-diols as the key step to set up the chiral carbon center with excellent enantiomeric excess. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Li, Bao-Sheng Wang, Yuhuang Proctor, Rupert S. J. Jin, Zhichao Chi, Yonggui Robin |
| format |
Article |
| author |
Li, Bao-Sheng Wang, Yuhuang Proctor, Rupert S. J. Jin, Zhichao Chi, Yonggui Robin |
| author_sort |
Li, Bao-Sheng |
| title |
Carbene-catalyzed desymmetrization of 1,3-diols: access to optically enriched tertiary alkyl chlorides |
| title_short |
Carbene-catalyzed desymmetrization of 1,3-diols: access to optically enriched tertiary alkyl chlorides |
| title_full |
Carbene-catalyzed desymmetrization of 1,3-diols: access to optically enriched tertiary alkyl chlorides |
| title_fullStr |
Carbene-catalyzed desymmetrization of 1,3-diols: access to optically enriched tertiary alkyl chlorides |
| title_full_unstemmed |
Carbene-catalyzed desymmetrization of 1,3-diols: access to optically enriched tertiary alkyl chlorides |
| title_sort |
carbene-catalyzed desymmetrization of 1,3-diols: access to optically enriched tertiary alkyl chlorides |
| publishDate |
2017 |
| url |
https://hdl.handle.net/10356/82223 http://hdl.handle.net/10220/43497 |
| _version_ |
1759853391722315776 |