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( R )‐2‐Isopropenylcyclopropane‐1,1‐dicarboxylic Acid: Absolute Configuration and Stereospecific Ring Expansion of Its Dimethyl Ester
Author(s) -
Quinkert Gerhard,
Schmalz HansGünther,
Walzer Egon,
Gross Stefan,
Dürner Gerd,
Bats Jan W.
Publication year - 1986
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198607321
Subject(s) - absolute configuration , stereospecificity , chirality (physics) , ring (chemistry) , chemistry , stereochemistry , dicarboxylic acid , salt (chemistry) , organic chemistry , chiral symmetry , catalysis , physics , quantum mechanics , nambu–jona lasinio model , quark
The predicted ( R ) sense of chirality of 1a has been substantiated by the X‐ray structure analysis of the salt formed from ent ‐ 1b and ( S )‐(–)‐1‐phenylethylamine. Compounds 1a and 1b , as well as the product mixtures 2a + 3a and 2b + 3b , which are formed by ring expansion, are valuable chiral precursors for the synthesis of natural products ( a , R = H; b , R = CH 3 ).