Nitrones by heterolytic fragmentation of .gamma.-N-hydroxyamino sulfonates. Conversion of a decahydroquinoline to a perhydroazaazulene
✍ Scribed by LeBel, Norman A.; Caprathe, Bradley W.
- Book ID
- 111912867
- Publisher
- American Chemical Society
- Year
- 1985
- Tongue
- English
- Weight
- 388 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0022-3263
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📜 SIMILAR VOLUMES
## Abstract An efficient methodology for the synthesis of α‐aminophosphonates has been developed taking advantage of the __tert__‐butyldimethylsilyl triflate activated addition of diethyl phosphite to __N__‐benzyl nitrones derived from chiral α‐alkoxy and α‐(Boc‐amino) aldehydes. The stereoselectiv
I) and addition of nitrones (II) results in a smooth condensation to give the unsaturated hydroxylamines (III) stereoselectively. These undergo reverse-Cope cyclizations at room temperature leading to the diastereomeric mixture of pyrrolidine-N-oxides (IV) and (V). -