Premium
The First In(OTf) 3 ‐Catalyzed Conversion of Kinetically Formed Homoallylic Alcohols into the Thermodynamically Preferred Regioisomers: Application to the Synthesis of 22 α ‐Sterols
Author(s) -
Loh TeckPeng,
Tan KuiThong,
Hu QiYing
Publication year - 2001
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 - 10.1002/1521-3773(20010803)40:15<2921::aid-anie2921>3.0.co;2-v
Subject(s) - structural isomer , aldehyde , catalysis , chemistry , computer science , combinatorial chemistry , stereochemistry , organic chemistry
A retro‐ene reaction that generates the parent aldehyde and a sigmatropic rearrangement are involved in the In(OTf) 3 ‐catalyzed conversion of homoallylic alcohols 1 into the thermodynamically favored regioisomers 2 . This method can be used for the stereocontrolled synthesis of linear homoallylic 22 α ‐sterols from their readily accessible branched 22 β isomers.