通过 Noyori 型还原探索β-羟基-γ-内酰胺的不对称合成范围。
Exploring the Scope of Asymmetric Synthesis of β-Hydroxy-γ-lactams via Noyori-type Reductions.
机构信息
Department of Chemistry, Analytical and Biological Chemistry Research Facility, Synthesis and Solid State Pharmaceutical Centre, University College Cork , Cork, Ireland.
Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research Facility, Synthesis and Solid State Pharmaceutical Centre, University College Cork , Cork, Ireland.
出版信息
Org Lett. 2016 Oct 7;18(19):4978-4981. doi: 10.1021/acs.orglett.6b02416. Epub 2016 Sep 22.
Enantio- and diastereoselective hydrogenation of β-keto-γ-lactams with a ruthenium-BINAP catalyst, involving dynamic kinetic resolution, has been employed to provide a general, asymmetric approach to β-hydroxy-γ-lactams, a structural motif common to several bioactive compounds. Full conversion to the desired β-hydroxy-γ-lactams was achieved with high diastereoselectivity (up to >98% de) by addition of catalytic HCl and LiCl, while β-branching of the ketone substituent demonstrated a pronounced effect on the modest to excellent enantioselectivity (up to 97% ee) obtained.
手性和非对映选择性氢化β-酮基-γ-内酰胺与钌-BINAP 催化剂，涉及动态动力学拆分，已被用于提供一种通用的、不对称的方法来制备β-羟基-γ-内酰胺，这是几种生物活性化合物的共同结构基序。通过添加催化量的 HCl 和 LiCl，可以完全转化为所需的β-羟基-γ-内酰胺，同时具有高非对映选择性（高达>98% de），而酮取代基的β-支化对获得的中等至优异的对映选择性（高达 97% ee）有显著影响。
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