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

Nels C. Gerstner; Christopher S. Adams; Maik Tretbar; Jennifer M. Schomaker

doi:10.1002/anie.201606195

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

Journal article

Peer reviewed

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

Nels C. Gerstner, Christopher S. Adams, Maik Tretbar and Jennifer M. Schomaker

Angewandte Chemie International Edition, Vol.55(42), pp.13240-13243

10/10/2016

DOI: 10.1002/anie.201606195

PMCID: PMC5218842

PMID: 27709816

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Abstract

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.

Chemistry

Chemistry, Multidisciplinary

Physical Sciences

Science & Technology

Details

Title: Subtitle: Stereocontrolled Syntheses of Seven-Membered Carbocycles by Tandem Allene Aziridination/[4+3] Reaction
Creators: Nels C. Gerstner - University of Wisconsin–Madison
Christopher S. Adams - University of Wisconsin–Madison
Maik Tretbar - University of Wisconsin–Madison
Jennifer M. Schomaker - University of Wisconsin–Madison
Resource Type: Journal article
Publication Details: Angewandte Chemie International Edition, Vol.55(42), pp.13240-13243
DOI: 10.1002/anie.201606195
PMID: 27709816
PMCID: PMC5218842
NLM abbreviation: Angew Chem Int Ed Engl
ISSN: 1433-7851
eISSN: 1521-3773
Publisher: Wiley
Number of pages: 4
Grant note: 1R01GM111412-01; RR08389-01; P41GM103399; S10RR08438; S10RR029220 / NIH; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA 1254397; CHE-9208463; CHE-9629688; BIR-0214394 / NSF; National Science Foundation (NSF) R01GM111412 / NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Institute of General Medical Sciences (NIGMS) S10RR008389 / NATIONAL CENTER FOR RESEARCH RESOURCES; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Center for Research Resources (NCRR)
Language: English
Date published: 10/10/2016
Academic Unit: Chemistry
Record Identifier: 9984934671002771

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