CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes
The copper hydride (CuH)-catalyzed enantioselective reduction of α,β-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of β-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolera...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
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American Chemical Society (ACS)
2020
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| Online Access: | https://hdl.handle.net/1721.1/126061 |
| _version_ | 1826212612700897280 |
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| author | Zhou, Yujing Bandar, Jeffrey Liu, Richard Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Zhou, Yujing Bandar, Jeffrey Liu, Richard Buchwald, Stephen Leffler |
| author_sort | Zhou, Yujing |
| collection | MIT |
| description | The copper hydride (CuH)-catalyzed enantioselective reduction of α,β-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of β-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed based on preliminary mechanistic studies and density functional theory calculations. |
| first_indexed | 2024-09-23T15:28:19Z |
| format | Article |
| id | mit-1721.1/126061 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T15:28:19Z |
| publishDate | 2020 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1260612022-10-02T02:46:08Z CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes Zhou, Yujing Bandar, Jeffrey Liu, Richard Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry The copper hydride (CuH)-catalyzed enantioselective reduction of α,β-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of β-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed based on preliminary mechanistic studies and density functional theory calculations. National Institutes of Health (U.S.) (Grant GM46059) National Institutes of Health (U.S.) (Grant GM122483) National Institutes of Health (U.S.) (Grant GM058160-17S1) National Institutes of Health (U.S.). Post-doctoral Fellowship (GM112197) 2020-07-07T14:18:34Z 2020-07-07T14:18:34Z 2018-01 2020-03-19T17:11:18Z Article http://purl.org/eprint/type/JournalArticle 0002-7863 https://hdl.handle.net/1721.1/126061 Zhou, Yujing et al. “CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes.” Journal of the American Chemical Society, vol. 140, no. 2, 2018, pp. 606-609 © 2018 The Author(s) en 10.1021/JACS.7B12260 Journal of the American Chemical Society Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) PMC |
| spellingShingle | Zhou, Yujing Bandar, Jeffrey Liu, Richard Buchwald, Stephen Leffler CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes |
| title | CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes |
| title_full | CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes |
| title_fullStr | CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes |
| title_full_unstemmed | CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes |
| title_short | CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes |
| title_sort | cuh catalyzed asymmetric reduction of α β unsaturated carboxylic acids to β chiral aldehydes |
| url | https://hdl.handle.net/1721.1/126061 |
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