Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 9, Pages 1285-1288Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201601612
Keywords
Allylation; Amides; Boron; Heterocycles; Spiro compounds
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- Grants-in-Aid for Scientific Research [15K21046, 15K05421] Funding Source: KAKEN
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Spirocycles are attractive synthetic targets for many synthetic chemists owing to their potent and promising biological activities. We previously reported a method for the highly enantioselective allylation of various isatins with beta-amido-functionalized allylstannanes under the influence of indium-based chiral catalysts and applied this method to the synthesis of 2-oxindole derivatives spiro-fused to an alpha-methylene-gamma-butyrolactone framework. In this communication, we report the successful development of a new catalytic system that enables en-antioselective tin-free amide allylation with the aid of a newly prepared (beta-amidoallyl) boronate for nucleophilic addition to isatins. This system consisting of a catalytic amount of diethyl-zinc as a competitive candidate in the presence of chiral 1,3-amino alcohols incorporating an acidic phenol functionality offers new opportunities for environmentally benign access to medicinally relevant spirocyclic 2-oxindoles.
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