Jung Cheol-Kyu, Garner Susan A, Krische Michael J
University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, USA.
Org Lett. 2006 Feb 2;8(3):519-22. doi: 10.1021/ol052859x.
[reaction: see text]. 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, FurPh2P, Fur2PhP, Fur3P). Hydrogen-labile functional groups, including alkynes, alkenes, benzylic ethers, and nitroarenes, remain intact under the coupling conditions.
[反应：见正文]。在环境温度和压力下，使用三-2-呋喃基膦配位的铑催化剂，在多种醛存在的情况下对甲基乙烯基酮（MVK）和乙基乙烯基酮（EVK）进行催化氢化反应，能够形成具有高非对映选择性水平的羟醛产物。当用2-呋喃基取代苯基（Ph3P、FurPh2P、Fur2PhP、Fur3P）时，非对映选择性会逐渐增加。包括炔烃、烯烃、苄基醚和硝基芳烃在内的对氢不稳定的官能团在偶联条件下保持完整。
