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Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis
Author(s) -
Greschner Wilko,
Neumann Beate,
Stammler HansGeorg,
Gröger Harald,
Kuck Dietmar
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201506906
Subject(s) - stereoselectivity , chemistry , stereochemistry , organic chemistry , catalysis
Inherently chiral acetophenones and benzaldehydes bearing the large, bowl‐shaped framework of tribenzotriquinacene (TBTQ) were synthesized in enantiomerically pure form employing enzyme catalysis. Five‐step sequences involving lipase CAL‐B lead to the (M)‐enantiomers, (+)‐2‐acetyl‐TBTQ (M)‐ 5 and (+)‐2‐formyl‐TBTQ (M)‐ 6 , whereas use of lipase PS leads to the (P)‐enantiomers, (−)‐2‐acetyl‐TBTQ (P)‐ 5 and (−)‐2‐formyl‐TBTQ (P)‐ 6 , with at least 99 % ee in each case. The absolute configuration of these rigid 3D building blocks was determined by X‐ray diffraction analysis of the ketones 5 and by comparison of their chiroptical properties with those of the aldehydes 6 .