在无需保护基的情况下，通过催化剂控制的 Wacker 型 homoallylic 醇氧化反应。
Catalyst-controlled Wacker-type oxidation of homoallylic alcohols in the absence of protecting groups.
机构信息
University of Utah, Department of Chemistry, 315 S. 1400 E, Salt Lake City, Utah 84112, USA.
出版信息
J Org Chem. 2011 May 6;76(9):3609-13. doi: 10.1021/jo200462a. Epub 2011 Apr 13.
Abstract
Homoallylic alcohols are oxidized to β-hydroxy ketones using a TBHP-mediated Pd-catalyzed Wacker-type oxidation. The use of a bidentate ligand, quinoline-2-oxazoline (Quinox), and TBHP((aq)) as the terminal oxidant provides good yields of the desired products with reaction times significantly reduced as compared to the Tsuji-Wacker oxidation. Additionally, bis- and tris-homoallylic alcohols are oxidized to provide cyclic peroxyketals, presumably via nucleophilic attack of the methyl ketone product.
摘要
使用 TBHP 介导的 Pd 催化的 Wacker 型氧化反应，将偕丙醇氧化为β-羟基酮。使用双齿配体喹喔啉-2-恶唑啉（Quinox）和 TBHP((aq)) 作为末端氧化剂，与 Tsuji-Wacker 氧化相比，可显著缩短反应时间，得到高产率的目标产物。此外，双和三偕丙醇被氧化为环状过氧缩醛，可能是通过甲基酮产物的亲核进攻。
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