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Protecting‐Group‐Free Synthesis of 3‐Amino‐3‐α‐prenyl‐oxindoles through the Direct Prenylation of Isatin‐Derived Imines
Author(s) -
Li DeFeng,
Jin HaiShan,
Zhang JingRu,
Jiang YiXuan,
Zhao LiMing
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800881
Subject(s) - prenylation , chemistry , isatin , bromide , combinatorial chemistry , zinc , imine , stereochemistry , organic chemistry , catalysis , enzyme
A zinc‐mediated α‐selective prenylation of isatin‐derived imine using prenyl bromide as the prenyl source in a sealed tube has been developed. The protocol enables an efficient access to various 3‐amino‐3‐α‐prenyl‐oxindoles from cheap and readily available chemicals in good to excellent yields. The obtained prenylated adduct can be further manipulated to other more complicated derivatives through cyclization or oxidation, which demonstrated the synthetic usefulness of this methodology. Additionally, we demonstrated that this zinc‐mediated methodology is also applicable to cinnamylation and geranylation.