Enantioselective Trifluoromethylthiolating Lactonization Catalyzed by an Indane-Based Chiral Sulfide
Enantioselective trifluoromethylthiolation, especially of alkenes, is a challenging task. In this work, we have developed an efficient approach for enantioselective trifluoromethylthiolating lactonization by designing an indane‐based bifunctional chiral sulfide catalyst and a shelf‐stable electrophi...
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| Published in | Angewandte Chemie International Edition Vol. 55; no. 19; pp. 5846 - 5850 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Blackwell Publishing Ltd
04.05.2016
Wiley Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Enantioselective trifluoromethylthiolation, especially of alkenes, is a challenging task. In this work, we have developed an efficient approach for enantioselective trifluoromethylthiolating lactonization by designing an indane‐based bifunctional chiral sulfide catalyst and a shelf‐stable electrophilic SCF3 reagent. The desired products were formed with diastereoselectivities of >99:1 and good to excellent enantioselectivities. The transformation represents the first enantioselective trifluoromethylthiolation of alkenes and the first enantioselective trifluoromethylthiolation that is enabled by a catalyst with a Lewis basic sulfur center.
An efficient approach for enantioselective trifluoromethylthiolating lactonization entails the use of an indane‐based bifunctional chiral sulfide catalyst and a new shelf‐stable electrophilic SCF3 reagent. This transformation represents the first enantioselective trifluoromethylthiolation that is enabled by a catalyst with a Lewis basic sulfur center. |
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| AbstractList | Enantioselective trifluoromethylthiolation, especially of alkenes, is a challenging task. In this work, we have developed an efficient approach for enantioselective trifluoromethylthiolating lactonization by designing an indane‐based bifunctional chiral sulfide catalyst and a shelf‐stable electrophilic SCF
3
reagent. The desired products were formed with diastereoselectivities of >99:1 and good to excellent enantioselectivities. The transformation represents the first enantioselective trifluoromethylthiolation of alkenes and the first enantioselective trifluoromethylthiolation that is enabled by a catalyst with a Lewis basic sulfur center. Enantioselective trifluoromethylthiolation, especially of alkenes, is a challenging task. In this work, we have developed an efficient approach for enantioselective trifluoromethylthiolating lactonization by designing an indane-based bifunctional chiral sulfide catalyst and a shelf-stable electrophilic SCF3 reagent. The desired products were formed with diastereoselectivities of >99:1 and good to excellent enantioselectivities. The transformation represents the first enantioselective trifluoromethylthiolation of alkenes and the first enantioselective trifluoromethylthiolation that is enabled by a catalyst with a Lewis basic sulfur center. Enantioselective trifluoromethylthiolation, especially of alkenes, is a challenging task. In this work, we have developed an efficient approach for enantioselective trifluoromethylthiolating lactonization by designing an indane‐based bifunctional chiral sulfide catalyst and a shelf‐stable electrophilic SCF3 reagent. The desired products were formed with diastereoselectivities of >99:1 and good to excellent enantioselectivities. The transformation represents the first enantioselective trifluoromethylthiolation of alkenes and the first enantioselective trifluoromethylthiolation that is enabled by a catalyst with a Lewis basic sulfur center. An efficient approach for enantioselective trifluoromethylthiolating lactonization entails the use of an indane‐based bifunctional chiral sulfide catalyst and a new shelf‐stable electrophilic SCF3 reagent. This transformation represents the first enantioselective trifluoromethylthiolation that is enabled by a catalyst with a Lewis basic sulfur center. Enantioselective trifluoromethylthiolation, especially of alkenes, is a challenging task. In this work, we have developed an efficient approach for enantioselective trifluoromethylthiolating lactonization by designing an indane-based bifunctional chiral sulfide catalyst and a shelf-stable electrophilic SCF3 reagent. The desired products were formed with diastereoselectivities of >99:1 and good to excellent enantioselectivities. The transformation represents the first enantioselective trifluoromethylthiolation of alkenes and the first enantioselective trifluoromethylthiolation that is enabled by a catalyst with a Lewis basic sulfur center.Enantioselective trifluoromethylthiolation, especially of alkenes, is a challenging task. In this work, we have developed an efficient approach for enantioselective trifluoromethylthiolating lactonization by designing an indane-based bifunctional chiral sulfide catalyst and a shelf-stable electrophilic SCF3 reagent. The desired products were formed with diastereoselectivities of >99:1 and good to excellent enantioselectivities. The transformation represents the first enantioselective trifluoromethylthiolation of alkenes and the first enantioselective trifluoromethylthiolation that is enabled by a catalyst with a Lewis basic sulfur center. |
| Author | An, Rui Zhang, Xuelin Liu, Xiang Zhao, Xiaodan Luo, Jie |
| Author_xml | – sequence: 1 givenname: Xiang surname: Liu fullname: Liu, Xiang organization: Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, 510275, Guangzhou, China – sequence: 2 givenname: Rui surname: An fullname: An, Rui organization: Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, 510275, Guangzhou, China – sequence: 3 givenname: Xuelin surname: Zhang fullname: Zhang, Xuelin organization: Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, 510275, Guangzhou, China – sequence: 4 givenname: Jie surname: Luo fullname: Luo, Jie organization: Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, 510275, Guangzhou, China – sequence: 5 givenname: Xiaodan surname: Zhao fullname: Zhao, Xiaodan email: zhaoxd3@mail.sysu.edu.cn organization: Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, 510275, Guangzhou, China |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27027644$$D View this record in MEDLINE/PubMed |
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| PublicationDate | May 4, 2016 |
| PublicationDateYYYYMMDD | 2016-05-04 |
| PublicationDate_xml | – month: 05 year: 2016 text: May 4, 2016 day: 04 |
| PublicationDecade | 2010 |
| PublicationPlace | WEINHEIM |
| PublicationPlace_xml | – name: WEINHEIM – name: Germany – name: Weinheim |
| PublicationTitle | Angewandte Chemie International Edition |
| PublicationTitleAbbrev | ANGEW CHEM INT EDIT |
| PublicationTitleAlternate | Angew. Chem. Int. Ed |
| PublicationYear | 2016 |
| Publisher | Blackwell Publishing Ltd Wiley Wiley Subscription Services, Inc |
| Publisher_xml | – name: Blackwell Publishing Ltd – name: Wiley – name: Wiley Subscription Services, Inc |
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(000375118500034.27) 2015; 127 Liu, JB (WOS:000315254500045) 2013; 15 Bootwicha, T (WOS:000327410300012) 2013; 52 Sheng, J (WOS:000335333700020) 2014; 50 Yang, YD (WOS:000320899200005) 2013; 135 Zhao, Y (WOS:000322835700023) 2013; 52 UMEMOTO, T (WOS:A1993KU90200009) 1993; 115 Denmark, S. E. (000375118500034.18) 2012; 124 Tlili, A (WOS:000320776900001) 2013; 52 Denmark, SE (WOS:000332684700047) 2014; 136 Purser, S (WOS:000252411800007) 2008; 37 Yang, T (WOS:000351393600069) 2015; 51 Shao, X. (000375118500034.55) 2013; 125 Wang, X. (000375118500034.64) 2013; 125 Zhao, Y. (000375118500034.84) 2013; 125 Chen, C. (000375118500034.12) 2012; 124 Yin, F (WOS:000331926800025) 2014; 16 Denmark, SE (WOS:000283955600060) 2010; 132 Lefebvre, Q (WOS:000336837900015) 2014; 50 Bootwicha, T. (000375118500034.8) 2013; 125 Chen, C (WOS:000300934700041) 2012; 51 Ferry, A (WOS:000261316100020) 2008; 73 Zhou, L (WOS:000291915100008) 2011; 133 Nikolaienko, P (WOS:000340257000005) 2014; 20 Besset, T (WOS:000346056600002) 2014; 20 Yang, Y (WOS:000308390100035) 2012; 77 Isanbor, C (WOS:000236926300001) 2006; 127 |
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| Snippet | Enantioselective trifluoromethylthiolation, especially of alkenes, is a challenging task. In this work, we have developed an efficient approach for... |
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| SubjectTerms | Alkenes asymmetric catalysis Chemistry Chemistry, Multidisciplinary chiral sulfides organocatalysis Physical Sciences Science & Technology Sulfides Sulfur trifluoromethylthiolation |
| Title | Enantioselective Trifluoromethylthiolating Lactonization Catalyzed by an Indane-Based Chiral Sulfide |
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