Department of Chemistry, New York University, New York, New York 10003, United States.
Org Lett. 2020 Nov 20;22(22):9075-9080. doi: 10.1021/acs.orglett.0c03439. Epub 2020 Nov 3.
Using a chiral (-)-menthone auxiliary, enantiopure cyclic derivatives of Baylis-Hillman adducts were synthesized. A diastereoselective peroxidation reaction was used to introduce an oxygen atom and establish another stereocenter. The resulting products could be elaborated by employing a one-flask reduction-acetylation protocol followed by a diastereoselective nucleophilic substitution reaction. Removal of the (-)-menthone auxiliary provided an enantiopure triol with a structure related to naturally occurring polyols.
使用手性(-)-薄荷酮助剂,合成了 Baylis-Hillman 加成物的对映纯环状衍生物。采用非对映选择性过氧化反应引入一个氧原子并建立另一个手性中心。所得产物可通过采用一锅还原-乙酰化法并随后进行非对映选择性亲核取代反应进行修饰。(-)-薄荷酮助剂的去除提供了一种具有与天然多元醇相关结构的对映纯三醇。