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Synthesis of cis , cis , cis , cis ‐[5.5.5.4]‐1‐Azafenestrane with Discovery of an Unexpected Dyotropic Rearrangement
Author(s) -
Denmark Scott E.,
Montgomery Justin I.
Publication year - 2005
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.200500367
Subject(s) - tandem , derivative (finance) , rearrangement reaction , chemistry , cycloaddition , nitroalkene , stereochemistry , cope rearrangement , catalysis , materials science , organic chemistry , enantioselective synthesis , financial economics , economics , composite material
An unprecedented skeletal reorganization initially hindered a concise route based on a tandem [4+2]/[3+2] nitroalkene cycloaddition for the synthesis of the strained title compound. Conditions to suppress the observed dyotropic rearrangement were developed, and X‐ray crystallographic analysis of the BF 3 derivative (see picture) of the azafenestrane revealed significant planarization around the central carbon atom.