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Novel concepts in directed biaryl synthesis, XXXIV. Synthesis, optical resolution, and helimerization of dinaphtho[2,1‐ b :1′,2′‐ d ]‐pyran‐4‐one
Author(s) -
Bringmann Gerhard,
Schöner Bernd,
Schupp Olaf,
Peters Karl,
Peters EvaMaria,
von Schnering Hans Georg
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940116
Subject(s) - chemistry , ring (chemistry) , nucleophile , pyran , resolution (logic) , lactone , stereochemistry , combinatorial chemistry , closure (psychology) , organic chemistry , catalysis , artificial intelligence , computer science , economics , market economy
A rational synthesis of the biaryl lactone 3 is described. This bridged biaryl, which gradually helimerizes at room temperature, could be synthesized in a non‐racemic form, chemically by atropo‐selective ring opening with a chiral O ‐nucleophile and subsequent ring closure, and chromatographically by HPLC on a chiral phase. For the enantiomerization process ( M )‐ 3 ⇄ ( P )‐ 3 , the activation parameters were determined.