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
收藏
页码：1066 / 1069
页数：4
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