Ward Dale E, Gillis H Martin, Akinnusi Olukayode T, Rasheed M Abdul, Saravanan K, Sasmal Pradip K
Department of Chemistry, University of Saskatchewan, Saskatoon, SK S7N 5C9, Canada.
Org Lett. 2006 Jun 8;8(12):2631-4. doi: 10.1021/ol060802k.
Meso 1,9-diketones (six to seven stereocenters) are readily obtained by stepwise or simultaneous two-directional aldol reactions of tetrahydro-4H-thiopyran-4-one with a thiopyran-derived aldehyde or dialdehyde. Enantioselective enolizations of these diketones with the lithium amide from (R,R)-bis(1-phenylethyl)amine occur with simultaneous kinetic resolution to give the mono-TMS enol ethers in >90% yields (BORSM) and >95% ee. The products are applicable to polypropionate synthesis. [reaction: see text]
中-1,9-二酮（六至七个立体中心）可通过四氢-4H-硫代吡喃-4-酮与硫代吡喃衍生的醛或二醛进行逐步或同时的双向羟醛反应轻松制得。这些二酮与(R,R)-双(1-苯乙基)胺的锂酰胺进行对映选择性烯醇化反应时，同时进行动力学拆分，以>90%的产率（BORSM）和>95%的对映体过量（ee）得到单-TMS烯醇醚。这些产物可用于聚丙酸酯的合成。[反应：见正文]
