A Hypervalent Iodide‐Initiated Fragment Coupling Cascade of  N ‐Allylhydrazones | Zendy

Lutz Kelly E. | Zendy; Thomson Regan J. | Zendy

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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.

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