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Stereocontrolled Syntheses of Seven‐Membered Carbocycles by Tandem Allene Aziridination/[4+3] Reaction
Author(s) -
Gerstner Nels C.,
Adams Christopher S.,
Tretbar Maik,
Schomaker Jennifer M.
Publication year - 2016
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.201606195
Subject(s) - allene , stereocenter , chemistry , tandem , sequence (biology) , stereochemistry , combinatorial chemistry , solvent , organic chemistry , enantioselective synthesis , catalysis , biochemistry , materials science , composite material
A tandem allene aziridination/[4+3]/reduction sequence converts simple homoallenic sulfamates into densely functionalized aminated cycloheptenes, where the relative stereochemistry at five contiguous asymmetric centers can be controlled through the choice of the solvent and the reductant. The products resulting from this chemistry can be readily transformed into complex molecular scaffolds which contain up to seven contiguous stereocenters.