Department of Chemistry, Chemistry Research Laboratory, University of Oxford , 12 Mansfield Road, Oxford, OX1 3TA, U.K.
Org Lett. 2014 Jun 20;16(12):3288-91. doi: 10.1021/ol501292x. Epub 2014 Jun 4.
The asymmetric synthesis of β-substituted lactones by catalytic asymmetric conjugate addition of alkyl groups to α,β-unsaturated lactones is reported. The method uses alkylzirconium nucleophiles prepared in situ from alkenes and the Schwartz reagent. Enantioselective additions to 6- and 7-membered lactones proceed at rt, tolerate a wide variety of functional groups, and are readily scalable. The method was used in a formal asymmetric synthesis of mitsugashiwalactone.
通过催化不对称共轭加成反应，将烷基基团添加到α，β-不饱和内酯中，实现了β-取代内酯的不对称合成。该方法使用烯烃原位制备的烷基锆亲核试剂和 Schwartz 试剂。对 6-和 7-元内酯的对映选择性加成反应在室温下进行，可耐受各种官能团，且易于规模化。该方法被用于mitsugashiwalactone 的正式不对称合成中。
