We report the synthesis and preliminary evaluation of (1S,2S,4R)-7,7-dimethyl-1-phenylbicyclo[2.2.1]heptan-2-ol 1a, which was obtained in 3 steps from inexpensive starting materials, as a chiral auxiliary. The potential for asymmetric induction was investigated by carrying out aza-Diels-Alder reactions with cyclopentadiene and imine derivatives of 1a from (R)-(+)-1-phenylethylamine, (S)-(−)-1-phenylethylamine and benzylamine. The results showed marked exo selectivity and good diastereoisomeric excess when 1a was combined with (R)-(+)-1-phenylethylamine. These results are comparable with those reported using (−)-8-phenylmenthol, suggesting that 1a can represent an economically viable alternative to current chiral auxiliaries.
Autori: | Fabris F. [Investigation] | |
Data di pubblicazione: | 2020 | |
Titolo: | endo-1-Phenylborneol as a novel, alternative chiral auxiliary for the aza-Diels-Alder reaction | |
Rivista: | TETRAHEDRON LETTERS | |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/j.tetlet.2020.152165 | |
Volume: | 61 | |
Appare nelle tipologie: | 2.1 Articolo su rivista |
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TetLett_2020.pdf | articolo principale | Documento in Post-print | Accesso gratuito (solo visione) | Riservato |