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Stereoselective Synthesis of Protected 1,2-Diols and 1,2,3-Triols by a Tandem Hydroboration−Coupling Sequence

✍ Scribed by Kapur, Manmohan; Khartulyari, Anton; Maier, Martin E.


Book ID
121713874
Publisher
American Chemical Society
Year
2006
Tongue
English
Weight
95 KB
Volume
8
Category
Article
ISSN
1523-7060

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Stereoselective synthesis of syn,syn-2-m
✍ Marta Galobardes; Marisa Mena; Pedro Romea; Fèlix Urpı́; Jaume Vilarrasa 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 77 KB

Chx 2 BCl-mediated syn-aldol reaction of the a-OTBS lactate-derived ketone 1 followed by in situ reduction of the resulting boron aldolate with LiBH 4 lead to complete stereoselectivity for the boronates 2 in 80-95% yields. Then, a very mild oxidative work-up of 2 (H 2 O 2 /NaOAc in THF-H 2 O) allow