Synthesis, Chiral Resolution, and Absolute Configuration of C2-Symmetric, Chiral 9,9′-Spirobifluorenes
Racemic 2,2′‐, 2,2′,7,7′‐, and 2,2′,3,3′‐substituted 9,9′‐spirobifluorenes were synthesised and successfully resolved by HPLC on a Chiralpak IA stationary phase on both analytical and semipreparative scales. Their absolute configurations were determined by comparison of their specific optical rotati...
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Published in | European journal of organic chemistry Vol. 2014; no. 29; pp. 6513 - 6518 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
01.10.2014
WILEY‐VCH Verlag Wiley Subscription Services, Inc |
Subjects | |
Online Access | Get full text |
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Summary: | Racemic 2,2′‐, 2,2′,7,7′‐, and 2,2′,3,3′‐substituted 9,9′‐spirobifluorenes were synthesised and successfully resolved by HPLC on a Chiralpak IA stationary phase on both analytical and semipreparative scales. Their absolute configurations were determined by comparison of their specific optical rotations with literature data or by comparison of retention times with independently prepared enantiopure material. These compounds are versatile C2‐symmetric building blocks for the formation of more sophisticated cleft‐like, chiral molecular architectures.
Dissymmetric difunctionalised 9,9′‐spirobifluorene derivatives were prepared and resolved by HPLC on a chiral stationary phase on a semipreparative scale. The absolute configurations of the resolved enantiomers were assigned by comparison of specific optical rotations with literature data or retention times of independently prepared enantiomerically pure material. |
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Bibliography: | ArticleID:EJOC201402738 istex:8FB53CCFF32EC6F2FD97D0E1EF87E073B36FB216 ark:/67375/WNG-B6PZPRSD-2 |
ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.201402738 |