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Hydroxy‐Directed, SmI 2 ‐Induced Conversion of Carbohydrates into Carbocycles
Author(s) -
Kan Toshiyuki,
Nara Shinji,
Ozawa Takashi,
Shirahama Haruhisa,
Matsuda Fuyuhiko
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000117)39:2<355::aid-anie355>3.0.co;2-u
Subject(s) - yield (engineering) , aldehyde , chemistry , derivative (finance) , stereochemistry , coupling (piping) , organic chemistry , catalysis , materials science , economics , financial economics , metallurgy
Polyoxygenated six‐membered carbocycles were derived from carbohydrates with complete stereocontrol through hydroxy‐directed coupling cyclization induced by SmI 2 . For example, the cis ‐1,3‐cyclohexanediol 3 is obtained from the D ‐glucopyranoside derivative 1 in excellent yield. The coupling cyclization is initiated by single‐electron transfer from SmI 2 to the formyl group of the δ ‐hydroxy aldehyde 2 generated in an equilibrium process.