Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer
| Autor: | Roly J. Armstrong, Adam Noble, Meganathan Nandakumar, Rafael M. P. Dias, Eddie L. Myers, Varinder K. Aggarwal |
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| Rok vydání: | 2018 |
| Předmět: |
Stereochemistry
Chemistry 010405 organic chemistry Communication boronic esters Allene Enantioselective synthesis General Chemistry General Medicine 010402 general chemistry 01 natural sciences Communications Catalysis Single isomer enantiodivergent reactions 0104 chemical sciences enantiospecific reactions chemistry.chemical_compound Allenes | Hot Paper elimination Stereospecificity allenes Axial chirality |
| Zdroj: | Angewandte Chemie International Edition Angewandte Chemie (International Ed. in English) Armstrong, R J, Nandakumar, M, Dias, R M P, Noble, A, Myers, E L & Aggarwal, V K 2018, ' Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer ', Angewandte Chemie-International Edition, vol. 57, no. 27, pp. 8203-8208 . https://doi.org/10.1002/anie.201804446 |
| ISSN: | 1433-7851 |
| DOI: | 10.1002/anie.201804446 |
| Popis: | An enantiodivergent method for the synthesis of multiply substituted allenes is described. Highly enantioenriched, point‐chiral boronic esters were synthesized by homologation of α‐seleno alkenyl boronic esters with lithiated carbamates and eliminated to form axially chiral allene products. By employing either oxidative or alkylative conditions, both syn and anti elimination could be achieved with complete stereospecificity. The process enables the synthesis of either M or P allenes from a single isomer of a point‐chiral precursor and can be employed for the enantioselective assembly of di‐, tri‐, and tetrasubstituted allenes. |
| Databáze: | OpenAIRE |
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