Palladium-Catalyzed [3,3] Sigmatropic Rearrangement of (Allyloxy)iminodiazaphospholidines: Allylic Transposition of CO and CN Functionality

A PVN to PVO interconversion is the thermodynamic driving force for the title reaction. Iminodiazaphospholidines 1 give phosphoramides 2, which are subsequently hydrolyzed under mild acidic conditions to yield primary or tosylamines 3. R=alkyl, phenyl; Ts=p‐toluenesulfonyl.

Saved in:

Bibliographic Details
Published in:	Angewandte Chemie International Edition Vol. 43; no. 14; pp. 1865 - 1868
Main Authors:	Lee, Ernest E., Batey, Robert A.
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 26-03-2004 WILEY‐VCH Verlag
Subjects:	allylic amines azides homogeneous catalysis palladium sigmatropic rearrangement
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	A PVN to PVO interconversion is the thermodynamic driving force for the title reaction. Iminodiazaphospholidines 1 give phosphoramides 2, which are subsequently hydrolyzed under mild acidic conditions to yield primary or tosylamines 3. R=alkyl, phenyl; Ts=p‐toluenesulfonyl.
Bibliography:	The Natural Science and Engineering Research Council (NSERC) of Canada funded this research. E.E.L. thanks the Ontario Ministry of Training for funding in the form of an Ontario Graduate Scholarship. R.A.B. gratefully acknowledges receipt of a Premier's Research Excellence Award. We also thank Dr. Alex Young for mass spectral analysis and Dr. Tim Burrow for NMR assistance. ark:/67375/WNG-M2K172WD-D istex:FD9FC7219BDDD6B0370026440BFE66F879E39A82 ArticleID:ANIE200353284 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200353284