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Rhodium(III)‐Catalyzed Allylic C(sp 3 )–H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles
Author(s) -
Archambeau Alexis,
Rovis Tomislav
Publication year - 2015
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.201504150
Subject(s) - allylic rearrangement , rhodium , catalysis , chemistry , alkyne , stereochemistry , medicinal chemistry , deuterium , organic chemistry , physics , quantum mechanics
Unsaturated N ‐sulfonamides undergo a Rh III ‐ catalyzed allylic C(sp 3 )H activation followed by insertion with an exogenous internal alkyne. The reaction generates [3.3.0], [4.3.0], and [5.3.0] azabicyclic structures with excellent diastereoselectivity. Deuterium labeling experiments implicate a 1,3‐Rh shift as a key step in the mechanism.
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