( R )‐2‐Isopropenylcyclopropane‐1,1‐dicarboxylic Acid: Absolute Configuration and Stereospecific Ring Expansion of Its Dimethyl Ester | Zendy

Quinkert Gerhard | Zendy; Schmalz HansGünther | Zendy; Walzer Egon | Zendy; Gross Stefan | Zendy; Dürner Gerd | Zendy; Bats Jan W. | Zendy

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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 ).

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