Moral John Alec, Moon Seong-Jin, Rodriguez-Torres Samuel, Minehan Thomas G
Department of Chemistry and Biochemistry, California State University-Northridge, Northridge, California 91330, USA.
Org Lett. 2009 Aug 20;11(16):3734-7. 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.
铟介导的醛与2-氯-3-碘丙烯的烯丙基化反应，随后与三芳基铟试剂或芳基硼酸进行钯催化的交叉偶联反应，能以良好至优异的产率和非对映选择性得到芳基取代的高烯丙醇。由与d-甘油醛丙酮化物进行的反应所得到的产物能够以高总产率转化为2-脱氧-β-C-芳基呋喃核糖苷。同样地，2-脱氧-β-C-芳基吡喃葡萄糖苷可以由2,4-O-亚苄基赤藓糖高效制备。
