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

A tandem allene aziridination/[4+3]/reduction sequence converts simple homoallenic sulfamates to 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...

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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
Online Access:Get full text
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Summary:A tandem allene aziridination/[4+3]/reduction sequence converts simple homoallenic sulfamates to 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 that contain up to seven contiguous stereocenters. A tandem allene aziridination/[4 + 3]/reduction sequence converts homoallenic sulfamates to aminated cycloheptanes, where the relative stereochemistry at five contiguous chiral carbons can be controlled through the choice of solvent and reductant.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201606195