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.
endo-1-Phenylborneol as a novel, alternative chiral auxiliary for the aza-Diels-Alder reaction / Bassani, M.; Scarso, A.; Drago, M.; Zambon, A.; Fabris, F.. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 61:31(2020), pp. 1-4. [10.1016/j.tetlet.2020.152165]
endo-1-Phenylborneol as a novel, alternative chiral auxiliary for the aza-Diels-Alder reaction
Bassani M.;Drago M.;Zambon A.
;
2020
Abstract
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.Pubblicazioni consigliate
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