期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 27, 页码 8203-8208出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201804446
关键词
allenes; boronic esters; elimination; enantiodivergent reactions; enantiospecific reactions
资金
- EPSRC [EP/I038071/1]
- Bristol University
- CAPES (Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior) Foundation [88881.120469/2016-01]
- EU [749862]
- Marie Curie Actions (MSCA) [749862] Funding Source: Marie Curie Actions (MSCA)
- Engineering and Physical Sciences Research Council [EP/K03927X/1] Funding Source: researchfish
- BBSRC [BB/F011539/1] Funding Source: UKRI
- EPSRC [EP/K03927X/1, EP/L011999/1, EP/I038071/1] Funding Source: UKRI
An enantiodivergent method for the synthesis of multiply substituted allenes is described. Highly enantioenriched, point-chiral boronic esters were synthesized by homologation of alpha-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 Pallenes from a single isomer of a point-chiral precursor and can be employed for the enantioselective assembly of di-, tri-, and tetrasubstituted allenes.
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