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Novel Carbocyclic Ring Closure of Hex‐5‐enopyranosides
Author(s) -
Das Sanjoy Kumar,
Mallet JeanMaurice,
Sinaÿ Pierre
Publication year - 1997
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.199704931
Subject(s) - chemistry , ring (chemistry) , cyclohexane , acetal , stereoselectivity , anomer , oxygen atom , stereochemistry , carbon atom , ether , vinyl ether , atom (system on chip) , carbon fibers , catalysis , organic chemistry , molecule , materials science , polymer , composite number , computer science , copolymer , composite material , embedded system
Retention of configuration at the anomeric carbon atom is observed for a novel rearrangement of carbohydrates. The readily accessible vinyl acetal 1 undergoes a triisobutylaluminum‐assisted, stereoselective transposition of an oxygen atom on the ring with an exocyclic carbon atom. This reaction provides a new entry to the highly functionalized cyclohexane 2 .