Synthesis of Enantiomerically Pure Dissymmetric 2,2'‐Disubstituted9,9'‐Spirobifluorenes
- 1 May 2005
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2005 (10) , 1991-2001
- https://doi.org/10.1002/ejoc.200400796
Abstract
Racemic dissymmetric 2,2'‐dihydroxy‐9,9'‐spirobifluorene was prepared and resolved by clathrate formation with (R,R)‐(+)‐2,3‐dimethoxy‐N,N,N',N'‐tetracyclohexylsuccindiamide, giving rise to both enantiomers in very good yields. The absolute stereochemistry of the resolved material could be assigned by an X‐ray structure analysis of single crystals of the clathrate. Enantiomerically pure diols could be transformed into the corresponding ditriflates, which were then used as starting materials in different cross‐coupling procedures to provide a number of new enantiomerically pure spiro compounds bearing versatile functional groups suitable for further elaboration, as demonstrated by some examples. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)Keywords
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