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Abstract
alpha,alpha-Disubstituted allylic pinacol boronic esters undergo highly selective allylborations of aldehydes to give tetrasubstituted homoallylic alcohols with exceptional levels of anti-Z-selectivity (>20:1). The scope of the reaction includes both acyclic and cyclic allylic boronic esters which lead to acyclic and exocyclic tetrasubstituted homoallylic alcohols. The use of beta-borylated allylic boronic esters gave fully substituted alkenes bearing a boronic ester which underwent further cross-coupling enabling a highly modular and stereo-selective approach to the synthesis of diaryl tetrasubstituted alkenes. Computational analysis revealed the origin of the remarkable selectivity observed.
Original language | English |
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Pages (from-to) | 6145-6149 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 53 |
Issue number | 24 |
Early online date | 5 May 2014 |
DOIs | |
Publication status | Published - 5 May 2014 |
Structured keywords
- BCS and TECS CDTs
Keywords
- alkenes
- allylation
- asymmetric synthesis
- C-C coupling
- synthetic methods
- ORIENTED ORGANIC-SYNTHESIS
- OXIDATIVE HECK ARYLATION
- STEREOSELECTIVE-SYNTHESIS
- TETRASUBSTITUTED ALKENES
- ENANTIOSELECTIVE SYNTHESIS
- HOMOALLYLIC ALCOHOLS
- DIASTEREOSELECTIVE SYNTHESIS
- SECONDARY ALCOHOLS
- REACTION SEQUENCE
- INTERNAL ALKYNES
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Dive into the research topics of 'Highly Selective Allylborations of Aldehydes Using alpha,alpha-Disubstituted Allylic Pinacol Boronic Esters'. Together they form a unique fingerprint.Projects
- 2 Finished
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Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
14/05/12 → 13/01/18
Project: Research