Protecting-Group-Free Synthesis of 3-tert-Prenylated Oxindoles: Contiguous All-Carbon Quaternary Centers via Tertiary Neopentyl Substitution

被引：53

作者：

Grant, Christopher D. ^{[1
]}

Krische, Michael J. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 20期

关键词：

ALDEHYDE OXIDATION LEVEL; C BOND FORMATION; TRANSFER HYDROGENATION; DISPLACEMENT-REACTIONS; REVERSE PRENYLATION; CLAISEN REARRANGEMENT; ISOROQUEFORTINE-C; ROQUEFORTINE-C; METAL REAGENTS; ALCOHOL;

D O I：

10.1021/ol9018562

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ruthenium-catalyzed tert-prenylation of isatin 1 occurs efficiently in the absence of N-protecting groups under the conditions of C-C bond-forming transfer hydrogenation employing 1,1-dimethylallene as the prenyl donor. The prenylated adduct, 3-hydroxy-3-tert-prenyl-oxindole 2, is converted to the tertiary neopentyl chloride 3, which participates in nucleophilic substitution by way of an aza-o-xylylene intermediate to furnish adducts 4a-4l. Through tertiary neopentyl substitution, two contiguous all-carbon quaternary centers are established.

引用

页码：4485 / 4487

页数：3

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