A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols
Reported is a rationally-designed one-pot sequential strategy that allows homoallylic alcohols to be employed in a catalytic, asymmetric, direct vinylogous aldol reaction with a series of activated acyclic ketones, including trifluoromethyl ketones, γ-ketoesters, and α-keto phosphonates, in high yie...
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| Format: | Article |
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MDPI AG
2016-06-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/21/7/842 |
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| author | Xufeng Hou Zhenzhong Jing Xiangbin Bai Zhiyong Jiang |
| author_facet | Xufeng Hou Zhenzhong Jing Xiangbin Bai Zhiyong Jiang |
| author_sort | Xufeng Hou |
| collection | DOAJ |
| description | Reported is a rationally-designed one-pot sequential strategy that allows homoallylic alcohols to be employed in a catalytic, asymmetric, direct vinylogous aldol reaction with a series of activated acyclic ketones, including trifluoromethyl ketones, γ-ketoesters, and α-keto phosphonates, in high yields (up to 95%) with excellent regio- and enantio-selectivity (up to 99% ee). This modular combination, including Jones oxidation and asymmetric organocatalysis, has satisfactory compatibility and reliability even at a 20 mmol scale, albeit without intermediary purification. |
| first_indexed | 2024-12-16T15:23:23Z |
| format | Article |
| id | doaj.art-35c52b99fb1442d0bfaff090f7a63b13 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-16T15:23:23Z |
| publishDate | 2016-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-35c52b99fb1442d0bfaff090f7a63b132022-12-21T22:26:32ZengMDPI AGMolecules1420-30492016-06-0121784210.3390/molecules21070842molecules21070842A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic AlcoholsXufeng Hou0Zhenzhong Jing1Xiangbin Bai2Zhiyong Jiang3School of Chemistry and Chemical Engineering, Xuchang University, Xuchang 461000, ChinaKey Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng 475004, Henan, ChinaKey Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng 475004, Henan, ChinaSchool of Chemistry and Chemical Engineering, Xuchang University, Xuchang 461000, ChinaReported is a rationally-designed one-pot sequential strategy that allows homoallylic alcohols to be employed in a catalytic, asymmetric, direct vinylogous aldol reaction with a series of activated acyclic ketones, including trifluoromethyl ketones, γ-ketoesters, and α-keto phosphonates, in high yields (up to 95%) with excellent regio- and enantio-selectivity (up to 99% ee). This modular combination, including Jones oxidation and asymmetric organocatalysis, has satisfactory compatibility and reliability even at a 20 mmol scale, albeit without intermediary purification.http://www.mdpi.com/1420-3049/21/7/842asymmetric organocatalysisvinylogous aldol reactionsoxidationcascadehomoallylic alcohols |
| spellingShingle | Xufeng Hou Zhenzhong Jing Xiangbin Bai Zhiyong Jiang A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols Molecules asymmetric organocatalysis vinylogous aldol reactions oxidation cascade homoallylic alcohols |
| title | A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols |
| title_full | A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols |
| title_fullStr | A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols |
| title_full_unstemmed | A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols |
| title_short | A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols |
| title_sort | one pot tandem strategy in catalytic asymmetric vinylogous aldol reaction of homoallylic alcohols |
| topic | asymmetric organocatalysis vinylogous aldol reactions oxidation cascade homoallylic alcohols |
| url | http://www.mdpi.com/1420-3049/21/7/842 |
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