Projects per year
Lithiation of carbamates followed by borylation provides a powerful method for the homologation of boron reagents. However, when applied to hindered systems (secondary carbamates with tBu-boronic esters) for the construction of two quaternary centers, this methodology fails. Instead, using mixed boranes (tBuBMe2), the synthesis of adjacent quaternary stereogenic centers with full stereocontrol was successful. The process can be repeated two or three times in one pot leading to carbon chains bearing multiple contiguous quaternary stereogenic centers. The boranes were converted into tertiary alcohols or C-tertiary amines using chloramine. The origin of the high selectivity for alkyl over Me group migration was determined computationally.
|Number of pages||4|
|Journal||Journal of the American Chemical Society|
|Publication status||Published - 17 Dec 2014|
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- 2 Finished
3-month Core Capability for Chemistry Research
1/01/13 → 1/04/13
Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
14/05/12 → 13/01/18
Professor Varinder K Aggarwal
- School of Chemistry - Alfred Capper Pass Chair of Chemistry
- Supramolecular and Mechanistic Chemistry
Person: Academic , Member