Resolution of a Configurationally Stable Hetero[4]helicene
We have developed an efficient chemical resolution of racemic hydroxy substituted dithia-aza[4]helicenes (DTA[4]H) <b>1(OH)</b> using enantiopure acids as resolving agents. The better diastereomeric separation was achieved on esters prepared with (1<i>S</i>)-(−)-camphanic aci...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-02-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/4/1160 |
| Summary: | We have developed an efficient chemical resolution of racemic hydroxy substituted dithia-aza[4]helicenes (DTA[4]H) <b>1(OH)</b> using enantiopure acids as resolving agents. The better diastereomeric separation was achieved on esters prepared with (1<i>S</i>)-(−)-camphanic acid. Subsequent simple manipulations produced highly optically pure (≥ 99% enantiomeric excess) (<i>P</i>) and (<i>M</i>)-<b>1(OH)</b> in good yields. The role of the position where the chiral auxiliary is inserted (<i>cape</i>- vs. <i>bay-zone</i>) and the structure of the enantiopure acid used on successful resolution are discussed. |
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| ISSN: | 1420-3049 |