Abstract
The first general method for the chemoselective synthesis of α,α-dideuterio alcohols directly from feedstock carboxylic acids under single electron transfer conditions using SmI2 is reported. This reaction proceeds after the activation of Sm(II) with a Lewis base, results in excellent levels of deuterium incorporation across a wide range of substrates, and represents an attractive alternative to processes mediated by pyrophoric alkali metal deuterides.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 5052-5055 |
| Number of pages | 4 |
| Journal | Organic letters |
| Volume | 16 |
| Issue number | 19 |
| DOIs | |
| State | Published - Oct 3 2014 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Szostak, M., Spain, M., & Procter, D. J. (2014). Selective synthesis of α,α-dideuterio alcohols by the reduction of carboxylic acids using Smi2 and D2O as deuterium source under set conditions. Organic letters, 16(19), 5052-5055. https://doi.org/10.1021/ol502404e