We have developed an efficient chemical resolution of racemic hydroxy substituted dithiaaza[ 4]helicenes (DTA[4]H) 1(OH) using enantiopure acids as resolving agents. The better diastereomeric separation was achieved on esters prepared with (1S)-()-camphanic acid. Subsequent simple manipulations produced highly optically pure ( 99% enantiomeric excess) (P) and (M)-1(OH) in good yields. The role of the position where the chiral auxiliary is inserted (cape- vs. bay-zone) and the structure of the enantiopure acid used on successful resolution are discussed.
Resolution of a Configurationally Stable Hetero[4]helicene
Abbate, Sergio;Longhi, Giovanna;
2022-01-01
Abstract
We have developed an efficient chemical resolution of racemic hydroxy substituted dithiaaza[ 4]helicenes (DTA[4]H) 1(OH) using enantiopure acids as resolving agents. The better diastereomeric separation was achieved on esters prepared with (1S)-()-camphanic acid. Subsequent simple manipulations produced highly optically pure ( 99% enantiomeric excess) (P) and (M)-1(OH) in good yields. The role of the position where the chiral auxiliary is inserted (cape- vs. bay-zone) and the structure of the enantiopure acid used on successful resolution are discussed.File in questo prodotto:
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