氘作为手性配体合成中立体化学不可见的阻断基团。
Deuterium as a Stereochemically Invisible Blocking Group for Chiral Ligand Synthesis.
机构信息
School of Chemistry, University of East Anglia , Norwich Research Park, Norwich NR4 7TU, U.K.
出版信息
Org Lett. 2017 Feb 3;19(3):702-705. doi: 10.1021/acs.orglett.6b03874. Epub 2017 Jan 24.
Highly diastereoselective lithiation (s-BuLi/TMEDA in EtO, -78 °C, 2 h) of (S)-2-ferrocenyl-4-(substituted)oxazolines followed by addition of MeOH-d gave up to 95% D incorporation. Subsequent application of alternative lithiation conditions (n-BuLi in THF, -78 °C, 2 h), followed by addition of an electrophile, resulted in a reversal of diastereoselectivity controlled primarily by the high k/k value for lithiation (isomer ratio typically between 10:1 and 20:1).
高度非对映选择性锂化（s-BuLi/TMEDA 在 EtO 中，-78°C，2 h）（S）-2-二茂铁基-4-（取代）恶唑啉，然后加入 MeOH-d，得到高达 95%的 D 含量。随后应用替代的锂化条件（n-BuLi 在 THF 中，-78°C，2 h），然后加入亲电试剂，导致非对映选择性反转，主要由锂化的高 k/k 值控制（异构体比通常在 10:1 和 20:1 之间）。
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