通过 2-丙醇介导的还原偶联催化对炔基醛的对映选择性烯丙基化反应。
Catalytic Enantioselective Allylations of Acetylenic Aldehydes via 2-Propanol-Mediated Reductive Coupling.
机构信息
Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , United States.
Institute of Chemistry, University of Campinas (UNICAMP) , P.O. Box 6154, CEP, 13083-970 Campinas , São Paulo , Brazil.
出版信息
Org Lett. 2018 Jul 6;20(13):4144-4147. doi: 10.1021/acs.orglett.8b01776. Epub 2018 Jun 25.
Abstract
Cyclometalated π-allyliridium C,O-benzoates modified by ( S)-SEGPHOS or ( S)-Cl,OMe-BIPHEP catalyze enantioselective 2-propanol-mediated reductive couplings of diverse nonmetallic allyl pronucleophiles with the acetylenic aldehyde TIPSC≡CCHO. Absolute stereochemistries of the resulting secondary homoallylic-propargylic alcohols were assigned using Rychnovsky's competing enantioselective conversion method.
摘要
(S)-SEGPHOS 或 (S)-Cl,OMe-BIPHEP 修饰的环金属化 π-烯丙基铱 C,O-苯甲酸盐催化剂可以催化各种非金属烯丙基给体与炔基醛 TIPSC≡CCHO 在仲醇介导的还原偶联反应中进行对映选择性反应。使用 Rychnovsky 的竞争对映选择性转化方法确定了生成的次级同烯丙基炔丙醇的绝对立体化学。
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