A hypervalent iodide-initiated fragment coupling cascade of N-allylhydrazones

Kelly E. Lutz; Regan James Thomson

doi:10.1002/anie.201100888

A hypervalent iodide-initiated fragment coupling cascade of N-allylhydrazones

Kelly E. Lutz, Regan James Thomson

Chemistry

Research output: Contribution to journal › Article › peer-review

36 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	4437-4440
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	19
DOIs	https://doi.org/10.1002/anie.201100888
State	Published - May 2 2011

Keywords

cascade reactions
hydrazones
hypervalent iodide reagents
stereoselective synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201100888

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A hypervalent iodide-initiated fragment coupling cascade of N-allylhydrazones

Abstract

Keywords

ASJC Scopus subject areas

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