An asymmetric dihydroxylation route to enantiomerically pure norfluoxetine and fluoxetine
β Scribed by Rajesh Kumar Pandey; Rodney A. Fernandes; Pradeep Kumar
- Book ID
- 104251260
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 68 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
An efficient, practical asymmetric synthesis of (R)-norfluoxetine 1 and (R)-fluoxetine 2 has been achieved. The synthetic strategy features a Sharpless asymmetric dihydroxylation (SAD) route to the common building block 1,3-amino alcohol 9, from which (R)-norfluoxetine, (R)-fluoxetine and other related analogs can be synthesized.
π SIMILAR VOLUMES
Successive treatment of chiral esters J\_ with LDA/Me3SiCl and NBS or NCS gave crystalline a-haloesters 2 which furnished halohydrins 4 and terminal epoxides 2 in high e.e.. The practical, chiral auxiliaries Xa and Xb (Scheme 1) confer high II-face differentiation to Diels-Alder-l and organocopper a
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