Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium:: High Syn-selectivity through the effect of tri-2-furylphosphine
Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium:: High Syn-selectivity through the effect of tri-2-furylphosphine
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DOI：
10.1021/ol052859x
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发表时间：
2006-02-02
期刊：
影响因子：
5.2
通讯作者：
Krische, MJ
中科院分区：
文献类型：
--
作者：
Jung, CK;Garner, SA;Krische, MJ
[图表]在环境温度和压力下，在各种醛的存在下，使用三-2-呋喃基膦连接的铑催化剂，甲基乙烯基酮（MVK）和乙基乙烯基酮（EVK）的催化氢化能够形成具有高水平的顺式-非对映选择性的羟醛产物。在用苯基残基顺序替换2-呋喃基残基（Ph 3 P、FurPh（2）P、Fur（2）PhP、Fur（3）P）后，观察到非对映选择性逐渐增加。氢不稳定官能团，包括炔、烯、苄醚和硝基芳烃，在偶联条件下保持完整。
[GRAPHICS]Catalytic hydrogenation of methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) in the presence of diverse aldehydes at ambient temperature and pressure using tri-2-furylphosphine-ligated rhodium catalysts enables formation of aldol products with high levels of syn-diastereoselectivity. A progressive increase in diastereoselectivity is observed upon sequential replacement of phenyl residues for 2-furyl residues (Ph3P, FurPh(2)P, Fur(2)PhP, Fur(3)P). Hydrogen-labile functional groups, including alkynes, alkenes, benzylic ethers, and nitroarenes, remain intact under the coupling conditions.