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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.
|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|
|Number of pages||26|
|ISBN (Print)||9783527667512, 9783527333431|
|Publication status||Published - 9 Apr 2014|
- BCS and TECS CDTs
- Total synthesis
FingerprintDive into the research topics of 'Lithium-Boron Chemistry: A Synergistic Strategy in Modern Synthesis'. Together they form a unique fingerprint.
- 3 Finished
Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
14/05/12 → 13/01/18
1/10/07 → 1/04/13