Protecting group directed asymmetric organocatalysis [3+2] cycloaddition of isocyanide and methyleneindolinone : stereoselective construction of spirocyclic oxindoles
The spiro[pyrrodilin-3,3’-oxindole] ring skeleton is a privileged structure with promising biological and pharmaceutical properties and only limited asymmetric synthetic approaches were reported due to the challenge in the synthesis of highly stereocontrolled quaternary carbon chiral centers. We...
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| Format: | Final Year Project |
| Language: | English |
| Published: |
2010
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| Subjects: | |
| Online Access: | http://hdl.handle.net/10356/39823 |
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| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | The spiro[pyrrodilin-3,3’-oxindole] ring skeleton is a privileged structure with
promising biological and pharmaceutical properties and only limited asymmetric
synthetic approaches were reported due to the challenge in the synthesis of highly
stereocontrolled quaternary carbon chiral centers. We developed a novel asymmetric
synthesis of spirocyclic oxindoles via [3+2] cycloaddition of isocyanide and
methyleneindolinone to afford adducts with two quaternary and one tertiary carbon
stereocenters in moderate to good yield and excellent enantioselectivities. We also
demonstrated that changing the protecting group of nitrogen atom in
methyleneindolenone can result in change of the absolute configuration of desired
spiro[pyrrodilin-3,3’-oxindole] core. |
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