Stereocontrolled Syntheses of Seven-Membered Carbocycles by Tandem Allene Aziridination/[4+3] Reaction

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 produc...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-10, Vol.55 (42), p.13240-13243
Main Authors: Gerstner, Nels C., Adams, Christopher S., Tretbar, Maik, Schomaker, Jennifer M.
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Allene
allenes
Aziridines - chemistry
Cyclization
cycloaddition
Cycloheptanes - chemical synthesis
Cycloheptanes - chemistry
heterocycles
Molecular Conformation
Nucleotide sequence
Oxidation-Reduction
rhodium
Scaffolds
Stereochemistry
Stereoisomerism
synthetic methods
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Summary: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. Magic seven: A tandem allene aziridination/[4+3]/reduction sequence converts homoallenic sulfamates into aminated cycloheptanes, where the relative stereochemistry at five contiguous chiral carbon atoms can be controlled through the choice of solvent. The resulting products can be readily transformed into complex molecular scaffolds that contain up to seven contiguous stereocenters.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201606195