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Stereoselective Substitution at Phenyl‐Substituted γ‐Lactols with Organometallic Compounds
Author(s) -
Schmitt Andreas,
Reißig HansUlrich
Publication year - 1995
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19951280904
Subject(s) - chemistry , tetrahydrofuran , stereoselectivity , nucleophilic substitution , selectivity , alkyl , medicinal chemistry , derivative (finance) , substitution reaction , substitution (logic) , nucleophile , organic chemistry , stereochemistry , catalysis , financial economics , economics , programming language , solvent , computer science
A variety of monosubstituted γ‐lactols 4–6 were prepared in good yields by DIBAL reduction of the corresponding γ‐lactones 1–3 . The monophenyl‐substituted lactols 4b–6b were transformed into disubstituted tetrahydrofuran derivatives by replacement of the hydroxyl group by the alkyl residue of organometallic compounds used as nucleophiles. The diastereoselectivity of the substitution was found to depend strongly on the substitution pattern of the γ‐lactols. For the reaction of the 3‐ and 4‐substituted derivatives 4b and 5b , respectively, good to excellent trans selectivity was observed, while the 5‐substituted derivative reacted without any diastereoselectivity. These results were interpreted by means of the Felkin‐Anh model.