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Complex of Tertiary Acetylenic Alcohol and Brucine or Sparteine. X‐Ray Crystal Structural Study and Application to Optical Resolution
Author(s) -
Toda Fumio,
Tanaka Koichi,
Ueda Hideo,
Ōshima Tokio
Publication year - 1985
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198500055
Subject(s) - brucine , chemistry , sparteine , alcohol , substituent , ring (chemistry) , resolution (logic) , hydrogen bond , stereochemistry , crystallography , molecule , organic chemistry , computer science , strychnine , biochemistry , artificial intelligence
Some tertiary acetylenic alcohols were optically resolved efficiently by complexation with brucine or sparteine. In the latter case, mutual optical resolution of sparteine and the tertiary acetylenic alcohol is possible. For an efficient resolution, the tertiary acetylenic alcohol should have at least one aromatic ring such as phenyl, naphthyl, thienyl as a substituent. The crystal structure of the 1:1 brucine complex and of the 1:1 (‐)‐sparteine complex of (‐)‐l‐( o ‐bromophenyl)‐1‐phenyl‐2‐propynol ( 1a ) are reported. In both cases, two hydrogen bonds,are important to fix the two components at a close position where mutual chiral recognition is efficient.