Diastereoselective addition of γ-alkylthio-allylboronates to aldehydes
✍ Scribed by Reinhard W. Hoffmann; Bruno Kemper
- Publisher
- Elsevier Science
- Year
- 1980
- Tongue
- French
- Weight
- 203 KB
- Volume
- 21
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
Both the (Z)-and the (E)-y-alkoxy-substituted allylboronates 1 and 3 have been prepared. They add to aldehydes with a diastereoselectivity generally exceeding 90% to give the syn-(2) and anti-diol derivatives 4, respectively. The structure of one of these adducts has been established by conversion i
The addition of allylboronates to sulfenimines gives homoallylsulfenamides which are potentially versatile intermediates for alkaloid synthesis.
We have developed a regioselective allylation and a regio-and diastereoselective crotylation of aldehydes with pyridin-2-yl sulfides. In the process, we have also optimized the diastereoselectivity of the addition of crotyl phenyl sulfide to aldehydes.