Diazoketone 5b, available in one step from proline benzyl ester, underwent conversion to quinolizidine gb with high diastereoseleOivity (19:1 gb/Tb) and in sm~risingly high enanfiomeric excess (75%). The key step presumably occurs via spirocyclic ylide 6b, which undergoes [l,2]-shift with retention.
✦ LIBER ✦
A Five-Step Synthesis of (±)-Tylophorine via a Nitrile-Stabilized Ammonium Ylide
✍ Scribed by Lahm, Günther; Stoye, Alexander; Opatz, Till
- Book ID
- 126224025
- Publisher
- American Chemical Society
- Year
- 2012
- Tongue
- English
- Weight
- 343 KB
- Volume
- 77
- Category
- Article
- ISSN
- 0022-3263
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