Premium
Phenylsulfonyl‐methylenation of aldonolactones
Author(s) -
Alzérreca Arnaldo,
Hernández Eliud,
Mangual Edgar,
Prieto José A.
Publication year - 1999
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570360236
Subject(s) - chemistry , lactol , boron trifluoride , sulfone , intramolecular force , derivative (finance) , dehydration , medicinal chemistry , trifluoride , organic chemistry , lactone , catalysis , biochemistry , financial economics , economics
The low temperature addition of dilithiomethylphenyl sulfone to 2,3‐ O ‐isopropylidene‐D‐erythronolactone, and to 5‐ O ‐( tert ‐butyldimethylsilyl)‐2,3‐ O ‐isopropylidene‐D‐ribofuranolactone gives the lactols 2 and 3a , respectively. Dehydration of lactol 2 in the presence of boron trifluoride etherate produces tetrahydrofuranylidene sulfones 5 and 6 in good yields. The reaction of lactol 3a under the same reaction conditions proceeds with formation of the 1′,5′‐anhydro derivative 7 via competing intramolecular substitution.