Synthesis of 3-Hydroxymethyl Isoindolinones via Cobalt-Catalyzed C(sp2)-H Carbonylation of Phenylglycinol Derivatives

被引：25
|
作者：
Lukasevics, Lukass [1 ]
Cizikovs, Aleksandrs [1 ]
Grigorjeva, Liene [1 ]
机构：
[1] Latvian Inst Organ Synth, LV-1006 Riga, Latvia
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 07期
关键词：
C-H ACTIVATION; REGIOSELECTIVE INTERMOLECULAR ANNULATION; DIRECTED FUNCTIONALIZATION; ASYMMETRIC-SYNTHESIS; SULFONAMIDES; ALKYNES; ACCESS; AMIDES; BONDS;
D O I：
10.1021/acs.orglett.0c00672
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the synthesis of 3-hydroxymethyl isoindolinones via cobalt-catalyzed C(sp(2))-H carbonylation of phenylglycinol derivatives using picolinamide as a traceless directing group is demonstrated. The reaction proceeds in the presence of a commercially available cobalt(II) tetramethylheptanedionate catalyst and employs DIAD as a "CO" surrogate. This synthetic route offers a broad substrate scope, excellent regioselectivity, and full preservation of the original stereochemistry. Besides, the developed method provides a pathway for accessing valuable enantiopure 3-substituted isoindolinone derivatives.
引用
收藏
页码：2720 / 2723
页数：4
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