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Synthesis of Chiral 4‐(ω‐Hydroxyalkyl)pyrazolidin‐3‐ones by Ring‐Chain Transformation of α‐Alkylidenelactones with Hydrazines
Author(s) -
Otto Andreas,
Ziemer Burkhard,
Liebscher Jürgen
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199811)1998:11<2667::aid-ejoc2667>3.0.co;2-r
Subject(s) - chemistry , enantiopure drug , ring (chemistry) , wittig reaction , stereoselectivity , transformation (genetics) , optically active , chain (unit) , side chain , stereochemistry , michael reaction , enantioselective synthesis , organic chemistry , combinatorial chemistry , catalysis , biochemistry , physics , astronomy , gene , polymer
Enantiopure α‐alkylidenelactones 7 were prepared by a Wittig reaction from α‐bromolactones 4 and chiral aldehydes 6 . Compounds 7 react with hydrazines 9 by stereoselective Michael‐like addition and ring–chain transformation affording optically active 4‐(ω‐hydroxyalkyl)pyrazolidin‐3‐ones 11 .