Optically Active Cyclopentanediol Synthetic Building Blocks from Tartaric Acid | Zendy

Bestmann Hans Jürgen | Zendy; Moenius Thomas | Zendy

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Optically Active Cyclopentanediol Synthetic Building Blocks from Tartaric Acid

Author(s) -

Bestmann Hans Jürgen,

Moenius Thomas

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.198609941

Subject(s) - cleavage (geology) , reagent , enantiomer , optically active , chemistry , tartaric acid , ring (chemistry) , nucleophile , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , catalysis , citric acid , fracture (geology) , composite material

Two enantiomeric five‐membered ring building blocks from the same educt : This was achieved by reaction of 1 with two different nucleophilic reagents. 1,4‐Addition of R 2 CuLi to 1 and cleavage of MeOH furnished ( R,R )‐ 2 ; 1,2‐Addition of RM to 1 , allyl rearrangement, and MeOH‐cleavage lead to the mirror image ( S,S )‐ 2 .

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