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. 2010 Jul 26;49(32):5529-32.
doi: 10.1002/anie.200906342.

Modular synthesis of 1,2-diamine derivatives by palladium-catalyzed aerobic oxidative cyclization of allylic sulfamides

Richard I McDonald  1 , Shannon S Stahl
Affiliations

Modular synthesis of 1,2-diamine derivatives by palladium-catalyzed aerobic oxidative cyclization of allylic sulfamides

Richard I McDonald et al. Angew Chem Int Ed Engl. .

Abstract

Allylic sulfamides undergo efficient aerobic oxidative cyclization at room temperature, mediated by a new Pd catalyst system consisting of 5% Pd(TFA)2/10% DMSO in THF. The synthetic utility of these reactions is enhanced by several features: (1) the sulfamide substrates are accessible in multi-gram scale from the corresponding allylic and primary amines, (2) the cyclic sulfamide products are readily converted to the corresponding 1,2-diamines upon treatment with LiAlH4, and (3) substrates derived from chiral allylic amines cyclize with very high levels of diastereoselectivity.

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Figures

Figure 1
Figure 1
Demonstration of 1,2-diamine synthesis via aerobic oxidative cyclization of a mannitol-derived allylic sulfamide.
Scheme 1
Scheme 1
Synthesis of 1,2-Diamines via Pd-Catalyzed Aerobic Oxidative Cyclization of Allylic Sulfamides.
Scheme 2
Scheme 2
Possible Mechanisms for the Pd-Catalyzed Oxidative Cylization Reaction.
See this image and copyright information in PMC

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