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Synthesis 2018; 50(22): 4444-4452
DOI: 10.1055/s-0036-1591574
DOI: 10.1055/s-0036-1591574
paper
Asymmetric Synthesis of Six-Membered Cyclic Sulfamides via Palladium-Catalyzed Alkene Carboamination Reactions
The authors thank the NIH (GM 071650) for financial support of this work. Z.J.G. wishes to thank Eli Lilly for a summer research fellowship and University of Michigan Rackham Graduate School for a Henry Earle Riggs Dissertation Fellowship. We acknowledge funding from NSF grant CHE-0840456 for X-ray diffractometer instrumentation.Further Information
Publication History
Received: 06 February 2018
Accepted after revision: 03 April 2018
Publication Date:
03 May 2018 (online)

Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65th birthday
Abstract
The asymmetric synthesis of six-membered cyclic sulfamides via palladium-catalyzed alkene carboamination reactions of N-homoallylsulfamides with aryl halides is described. High levels of enantioselectivity were obtained with a catalyst composed of Pd2dba3 and (S)-Siphos-PE.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591574.
- Supporting Information
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For selected examples of the use of 1,3-diamines in asymmetric synthesis, see:
For the synthesis of five-membered cyclic sulfamides, see:
For reviews on Pd-catalyzed alkene carboamination or carboalkoxylation reactions between aryl/alkenyl halides/triflates and alkenes bearing tethered nucleophiles, see:
For studies on the mechanism of syn-migratory insertion of alkenes into Pd–N bonds, see: