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α-Lithiation–Electrophile Trapping of N -Thiopivaloylazetidin-3-ol: Stereoselective Synthesis of 2-Substituted 3-Hydroxyazetidines

✍ Scribed by Hodgson, David M.; Pearson, Christopher I.; Thompson, Amber L.


Book ID
120642986
Publisher
American Chemical Society
Year
2013
Tongue
English
Weight
685 KB
Volume
78
Category
Article
ISSN
0022-3263

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✍ Annett Bartels; Peter G. Jones; Jürgen Liebscher 📂 Article 📅 1997 🏛 Elsevier Science 🌐 English ⚖ 246 KB

Michael-addition of nitromethane anion to 5-ylidene-1,3-dioxane-4-ones 2 gives high yields of 5-(13-nitroalkyl)-l,3-dioxane-4-ones 3 and 4 with a preponderance of 3 (reattack). Hydrogenation of the products in the presence of Raney-Ni affords optically active 4-substituted cis-3-(o~-hydroxyethyl)-py