Palladium Catalyzed Asymmetric Allylation of 3-OBoc-Oxindoles: An Efficient Synthesis of 3-Allyl-3-hydroxyoxindoles

被引：42

作者：

Jayakumar, Samydurai ^{[1
]}

Kumarswamyreddy, Nandarapu ^{[1
]}

Prakash, Muthuraj ^{[1
]}

Kesavan, Venkitasamy ^{[1
]}

机构：

[1] Indian Inst Technol, Bhupat & Jyothi Mehta Sch Biosci, Dept Biotechnol, Biol Chem Lab, Madras 600036, Tamil Nadu, India

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 05期

关键词：

CARBON QUATERNARY STEREOCENTERS; VINYLOGOUS ALDOL REACTION; ALLYLIC ALKYLATION; ENANTIOSELECTIVE ALLYLATION; 3-SUBSTITUTED; 3-HYDROXY-2-OXINDOLES; MOLECULAR-OXYGEN; TARTARIC ACID; DIRECT ACCESS; ISATINS; CONSTRUCTION;

D O I：

10.1021/acs.orglett.5b00034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Allyl-3-hydroxyoxindoles were synthesized in very good enantio- (up to 97% ee) and diastereoselectivities (dr up to 7.6:1) with contiguous quaternary and tertiary stereogenic centers by employing tartrate derived bi(oxazoline) in Pd-catalyzed allylation of 3-OBoc-oxindole. Synthetic utility of 3-allyl-3-hydroxyoxindole was demonstrated by synthesizing a highly substituted spiro(oxindole-3,2'-tetrahydrofuran) derivative in good yield and stereoselectivity.

引用

页码：1066 / 1069

页数：4

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