Abstract
Reduction of carbonyl functionality into a hydroxyl moiety1 has been studied with both Lewis base2 and Lewis acid3 mediated hydrosilylation protocols. As part of an ongoing research investigating the intramolecular hydride delivery of a pinacol-derived chlorosilane, we seek to explore the Lewis acidity of hydrosilyl ethers derived from this novel cyclic chlorosilane in Lewis base activated systems for the anchimeric assistance reduction of carbonyl compounds.
Reduction of salicylaldehyde to salicyl alcohol was achieved in 70% upon use of trimethylamine as Lewis base and hydrochloric acid capturing agent. Screening of other Lewis bases (PPh3, DBU, Hünig’s base, Pyridine, Pyridine N-oxide, HMPA, etc) and optimization of reaction conditions with the newly developed chlorosilane will be presented.
Reduction of salicylaldehyde to salicyl alcohol was achieved in 70% upon use of trimethylamine as Lewis base and hydrochloric acid capturing agent. Screening of other Lewis bases (PPh3, DBU, Hünig’s base, Pyridine, Pyridine N-oxide, HMPA, etc) and optimization of reaction conditions with the newly developed chlorosilane will be presented.
| Original language | English |
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| Publication status | Published - 27 Aug 2017 |
| Publication type | Not Eligible |
| Event | SWISS SUMMER SCHOOL 2017: TRENDS IN ORGANIC SYNTHESIS - EUROTEL-VICTORIA, VILLARS SUN OLLON, Switzerland Duration: 27 Aug 2017 → 31 Aug 2017 http://scg.ch/index.php?option=com_content&view=article&id=1648:swiss-summer-school-2017-trends-in-organic-synthesis-august-27-31-2017&catid=74:fr-news&Itemid=244&lang=en |
Conference
| Conference | SWISS SUMMER SCHOOL 2017 |
|---|---|
| Country/Territory | Switzerland |
| City | VILLARS SUN OLLON |
| Period | 27/08/17 → 31/08/17 |
| Internet address |