Asymmetric conjugate addition of grignard reagents to 3-silyl unsaturated esters for the facile preparation of enantioenriched β-silylcarbonyl compounds and allylic silanes
A highly enantioselective conjugate addition of Grignard reagents to 3-silyl unsaturated esters to deliver synthetically useful chiral β-silylcarbonyl compounds was developed. The synthetic value of this methodology was further illustrated by the synthesis of enantioenriched β-hydroxyl esters and th...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2015
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| Online Access: | https://hdl.handle.net/10356/96686 http://hdl.handle.net/10220/38502 |
| _version_ | 1811691471069249536 |
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| author | Zhao, Kai Loh, Teck-Peng |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Zhao, Kai Loh, Teck-Peng |
| author_sort | Zhao, Kai |
| collection | NTU |
| description | A highly enantioselective conjugate addition of Grignard reagents to 3-silyl unsaturated esters to deliver synthetically useful chiral β-silylcarbonyl compounds was developed. The synthetic value of this methodology was further illustrated by the synthesis of enantioenriched β-hydroxyl esters and the facile access granted to various α-chiral allylic silanes. A plethora of diastereoselective transformations of β-silylenolates were also investigated and afforded manifold organosilanes that contained contiguous stereogenic centers with excellent enantioselectivity. |
| first_indexed | 2024-10-01T06:20:25Z |
| format | Journal Article |
| id | ntu-10356/96686 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:20:25Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-10356/966862020-03-07T12:31:21Z Asymmetric conjugate addition of grignard reagents to 3-silyl unsaturated esters for the facile preparation of enantioenriched β-silylcarbonyl compounds and allylic silanes Zhao, Kai Loh, Teck-Peng School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry A highly enantioselective conjugate addition of Grignard reagents to 3-silyl unsaturated esters to deliver synthetically useful chiral β-silylcarbonyl compounds was developed. The synthetic value of this methodology was further illustrated by the synthesis of enantioenriched β-hydroxyl esters and the facile access granted to various α-chiral allylic silanes. A plethora of diastereoselective transformations of β-silylenolates were also investigated and afforded manifold organosilanes that contained contiguous stereogenic centers with excellent enantioselectivity. 2015-08-24T05:08:34Z 2019-12-06T19:33:56Z 2015-08-24T05:08:34Z 2019-12-06T19:33:56Z 2014 2014 Journal Article Zhao, K., & Loh, T.-P. (2014). Asymmetric conjugate addition of grignard reagents to 3-silyl unsaturated esters for the facile preparation of enantioenriched β-silylcarbonyl compounds and allylic silanes. Chemistry - A European Journal, 20(50), 16764-16772. 0947-6539 https://hdl.handle.net/10356/96686 http://hdl.handle.net/10220/38502 10.1002/chem.201403849 en Chemistry - A European Journal © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry Zhao, Kai Loh, Teck-Peng Asymmetric conjugate addition of grignard reagents to 3-silyl unsaturated esters for the facile preparation of enantioenriched β-silylcarbonyl compounds and allylic silanes |
| title | Asymmetric conjugate addition of grignard reagents to 3-silyl unsaturated esters for the facile preparation of enantioenriched β-silylcarbonyl compounds and allylic silanes |
| title_full | Asymmetric conjugate addition of grignard reagents to 3-silyl unsaturated esters for the facile preparation of enantioenriched β-silylcarbonyl compounds and allylic silanes |
| title_fullStr | Asymmetric conjugate addition of grignard reagents to 3-silyl unsaturated esters for the facile preparation of enantioenriched β-silylcarbonyl compounds and allylic silanes |
| title_full_unstemmed | Asymmetric conjugate addition of grignard reagents to 3-silyl unsaturated esters for the facile preparation of enantioenriched β-silylcarbonyl compounds and allylic silanes |
| title_short | Asymmetric conjugate addition of grignard reagents to 3-silyl unsaturated esters for the facile preparation of enantioenriched β-silylcarbonyl compounds and allylic silanes |
| title_sort | asymmetric conjugate addition of grignard reagents to 3 silyl unsaturated esters for the facile preparation of enantioenriched β silylcarbonyl compounds and allylic silanes |
| topic | DRNTU::Science::Chemistry::Organic chemistry |
| url | https://hdl.handle.net/10356/96686 http://hdl.handle.net/10220/38502 |
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