A Sequential Indium-Mediated Aldehyde Allylation/Palladium-Catalyzed Cross-Coupling Reaction in the Synthesis of 2-Deoxy-beta-C-Aryl Glycosides

作者：Moral John Alec; Moon Seong Jin; Rodriguez Torres Samuel; Minehan Thomas G^*

来源：Organic Letters, 2009, 11(16): 3734-3737.

DOI：10.1021/ol901353f

Indium-mediated allylation of aldehydes with 2-chloro-3-iodopropene, followed by a palladium-catalyzed cross-coupling reaction with triarylindium reagents or arylboronic acids, leads to aryl-substituted homoallylic alcohols in good to excellent yields and diastereoselectivities. The products obtained from reactions conducted with D-glyceraldehyde acetonide can be transformed into 2-deoxy-beta-C-aryl ribofuranosides in high overall yields. Similarly, 2-deoxy-beta-C-aryl allopyranosides may be prepared efficiently from 2,4-O-benzylidene erythrose.

• 出版日期2009-8-20