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Synthesis of Substituted 1,5‐Dioxaspiro[2.4]heptanes from 2,3‐ Dichloroprop‐1‐ene
Author(s) -
Alonso Francisco,
Meléndez Jaisiel,
Yus Miguel
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200210)85:10<3262::aid-hlca3262>3.0.co;2-r
Subject(s) - chemistry , ene reaction , methylene , biphenyl , catalysis , medicinal chemistry , stereochemistry , organic chemistry , combinatorial chemistry
The 4,4′‐di( tert ‐butyl)biphenyl(DTBB)‐catalyzed lithiation of 2,3‐dichloroprop‐1‐ene ( 10 ) in THF at 0°, in the presence of symmetrically substituted ketones, led to the corresponding methylene‐substituted diols 11 ( Scheme 2 ), which, by treatment with NaH and I 2 in THF at room temperature, furnished a series of 1,5‐dioxaspiro[2.4]heptanes 14 ( Scheme 4 ). Oxidation of compounds 14 with RuO 4 gave the corresponding lactones 16 . Compounds 14 and 16 are structural units present in many biologically active natural compounds and in versatile intermediates in synthetic organic chemistry.