Enantioselective Synthesis of Spirooxindole α-exo-Methylene-γ-butyrolactones from 3-OBoc-Oxindoles

Chiral Lewis bases facilitated the synthesis of highly functionalized spirooxindoles containing α‐exo‐methylene‐γ‐butyrolactones in high yields (76–92 %) and excellent enantioselectivities (up to 98 % ee) at ambient temperature. An efficient method was developed for the synthesis of spirooxindole α‐...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-03, Vol.2014 (9), p.1893-1898
Main Authors: Jayakumar, Samydurai, Muthusamy, Subramaniam, Prakash, Muthuraj, Kesavan, Venkitasamy
Format: Article
Language:English
Subjects:
Allylic alkylation
Asymmetric catalysis
Lewis bases
Organocatalysis
Spiro compounds
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Summary:Chiral Lewis bases facilitated the synthesis of highly functionalized spirooxindoles containing α‐exo‐methylene‐γ‐butyrolactones in high yields (76–92 %) and excellent enantioselectivities (up to 98 % ee) at ambient temperature. An efficient method was developed for the synthesis of spirooxindole α‐exo‐methylene‐γ‐butyrolactone in good yield and excellent diastereoselectivity and enantioselectivity with a broad range of substrates.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201301684