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Synthesis of Enantiomerically Pure Dissymmetric 2,2'‐Disubstituted9,9'‐Spirobifluorenes
Author(s) -
Thiemann Frank,
Piehler Torsten,
Haase Detlev,
Saak Wolfgang,
Lützen Arne
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400796
Subject(s) - chemistry , clathrate hydrate , enantiomer , stereochemistry , organic chemistry , hydrate
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)