Stereoselective synthesis of syn-1,3-diol acetonides by reductive decyanation of cyanohydrins
β Scribed by Rychnovsky, Scott D.; Zeller, Sam; Skalitzky, Donald J.; Griesgraber, George
- Book ID
- 127196801
- Publisher
- American Chemical Society
- Year
- 1990
- Tongue
- English
- Weight
- 249 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
The diastereoselective reduction of acyclic B-alkoxy ketones with lithium aluminum hydride in the presence of lithium iodide has been studied and found to provide syn-1,3-diol derivatives with high diastereoselection. -The stereocontrolled formation of 1,3-diols is of great interest to synthetic che
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