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The dimesitylboron group in organic synthesis 7. A unique variant of the Boron-Wittig reaction which stereoselectively yields 1,2-diols

✍ Scribed by Andrew Pelter; Dieter Buss; Andrew Pitchford

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 213 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80861-3

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✦ Synopsis

Low temperature oxidation of the intermediates in the Wittig reactions of aryl aldehydes with carbanions stabilised with an adjacent dimesitylboron group leads stereoselectively to erythro-1,2-diols. The mechanistic implications for the boron-Wittig reactions are discussed.

📜 SIMILAR VOLUMES

Hindered organoboron groups in organic s

Hindered organoboron groups in organic synthesis. 13. The direct production of ketones from aliphatic aldehydes by a unique variant of the boron-wittig reaction

✍ Andrew Pelter; Keith Smith; Said Elgendy; Martin Rowlands 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 230 KB

In the presence of trifluoroacetic anhydride or N-chlorosuccinimide, aliphatic aldehydes react with dimesitylboron stabilised carbanions to give, after work up, the corresponding ketones, a process which is unique among Wittig type reactions. Yields of ketones are satisfactory in all cases