A four-component reaction for the synthesis of dioxadiazaborocines
A four-component reaction for the synthesis of heterocyclic boronates is reported. Readily available hydrazides, α-hydroxy aldehydes, and two orthogonally reactive boronic acids are combined in a single step to give structurally distinct bicyclic boronates, termed dioxadiazaborocines (DODA borocines...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2015
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/105983 http://hdl.handle.net/10220/26036 http://dx.doi.org/10.1002/anie.201502989 |
| _version_ | 1826117350547521536 |
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| author | Flagstad, Thomas Petersen, Mette Terp Nielsen, Thomas Eiland |
| author2 | Singapore Centre for Environmental Life Sciences Engineering |
| author_facet | Singapore Centre for Environmental Life Sciences Engineering Flagstad, Thomas Petersen, Mette Terp Nielsen, Thomas Eiland |
| author_sort | Flagstad, Thomas |
| collection | NTU |
| description | A four-component reaction for the synthesis of heterocyclic boronates is reported. Readily available hydrazides, α-hydroxy aldehydes, and two orthogonally reactive boronic acids are combined in a single step to give structurally distinct bicyclic boronates, termed dioxadiazaborocines (DODA borocines). In this remarkable process, one boronic acid reacts as a carbon nucleophile and the other as a boron electrophile to provide enantio- and diastereomerically pure heterocyclic boronates with multiple stereocenters in high yields. |
| first_indexed | 2024-10-01T04:25:50Z |
| format | Journal Article |
| id | ntu-10356/105983 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:25:50Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-10356/1059832019-12-06T22:02:10Z A four-component reaction for the synthesis of dioxadiazaborocines Flagstad, Thomas Petersen, Mette Terp Nielsen, Thomas Eiland Singapore Centre for Environmental Life Sciences Engineering DRNTU::Science::Chemistry A four-component reaction for the synthesis of heterocyclic boronates is reported. Readily available hydrazides, α-hydroxy aldehydes, and two orthogonally reactive boronic acids are combined in a single step to give structurally distinct bicyclic boronates, termed dioxadiazaborocines (DODA borocines). In this remarkable process, one boronic acid reacts as a carbon nucleophile and the other as a boron electrophile to provide enantio- and diastereomerically pure heterocyclic boronates with multiple stereocenters in high yields. 2015-06-23T07:47:16Z 2019-12-06T22:02:10Z 2015-06-23T07:47:16Z 2019-12-06T22:02:10Z 2015 2015 Journal Article Flagstad, T., Petersen, M. T., & Nielsen, T. E. (2015). A Four-Component Reaction for the Synthesis of Dioxadiazaborocines. Angewandte Chemie International Edition, 54(29), 8395-8397. 1433-7851 https://hdl.handle.net/10356/105983 http://hdl.handle.net/10220/26036 http://dx.doi.org/10.1002/anie.201502989 en Angewandte Chemie International Edition © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry Flagstad, Thomas Petersen, Mette Terp Nielsen, Thomas Eiland A four-component reaction for the synthesis of dioxadiazaborocines |
| title | A four-component reaction for the synthesis of dioxadiazaborocines |
| title_full | A four-component reaction for the synthesis of dioxadiazaborocines |
| title_fullStr | A four-component reaction for the synthesis of dioxadiazaborocines |
| title_full_unstemmed | A four-component reaction for the synthesis of dioxadiazaborocines |
| title_short | A four-component reaction for the synthesis of dioxadiazaborocines |
| title_sort | four component reaction for the synthesis of dioxadiazaborocines |
| topic | DRNTU::Science::Chemistry |
| url | https://hdl.handle.net/10356/105983 http://hdl.handle.net/10220/26036 http://dx.doi.org/10.1002/anie.201502989 |
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