Projects per year
Abstract
Organoboranes and boronic esters react with nucleophiles to give an intermediate boronate complex. If the nucleophile contains a good enough leaving group, a 1,2-metallate rearrangement takes places resulting in the homologation of the starting boron species. A broad range of achiral and chiral organoborons can be homologated using enantioenriched lithiated carbamates with excellent stereospecificity. The homologated chiral boron species can then undergo further homologations, often in a one-pot process, or be converted into alternative functional groups. The factors responsible for stereocontrol are described and applications of the methodology in total synthesis are illustrated.
Original language | English |
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Title of host publication | Lithium Compounds in Organic Synthesis |
Subtitle of host publication | From Fundamentals to Applications |
Editors | R. Luisi, V. Capriati |
Place of Publication | Weinheim, Germany |
Publisher | Wiley-Blackwell |
Pages | 397-422 |
Number of pages | 26 |
ISBN (Print) | 9783527667512, 9783527333431 |
DOIs | |
Publication status | Published - 9 Apr 2014 |
Research Groups and Themes
- BCS and TECS CDTs
Keywords
- Borylation
- Carbamates
- Carbenoids
- Lithiation
- Organolithiums
- Stereospecific
- Total synthesis
Fingerprint
Dive into the research topics of 'Lithium-Boron Chemistry: A Synergistic Strategy in Modern Synthesis'. Together they form a unique fingerprint.Projects
- 3 Finished
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3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
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Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
Aggarwal, V. K. (Principal Investigator)
14/05/12 → 13/01/18
Project: Research
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GENERAL AND CONVERGENT STRATEGY FOR ASYMMETRIC SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/07 → 1/04/13
Project: Research