Premium
A Hypervalent Iodide‐Initiated Fragment Coupling Cascade of N ‐Allylhydrazones
Author(s) -
Lutz Kelly E.,
Thomson Regan J.
Publication year - 2011
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/anie.201100888
Subject(s) - hypervalent molecule , hydrazone , stereocenter , cascade , iodide , chemistry , allylic rearrangement , alkene , aldehyde , adduct , ether , natural product , stereochemistry , combinatorial chemistry , organic chemistry , iodine , enantioselective synthesis , catalysis , chromatography
Highway to the hydrazone : A hypervalent iodide initiated cascade process enables the rapid union of an aldehyde, an allylic hydrazide, and an alcohol (see scheme; Pv=pivaloyl). This process affords a diverse range of functionalized ether adducts, while simultaneously generating a stereodefined alkene and two new vicinal stereocenters. The use of chiral non‐racemic hydrazines and alcohols offers a rapid entry to complex “natural product‐like” structures.