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Synthesis and reactivity of unique heterocyclic structures en route to substituted diamines.

ABSTRACT: Rhodium-catalyzed oxidative cyclization of allylic hydroxylamine-derived sulfamate esters furnishes a novel family of bicyclic aziridines that serve as functional precursors to substituted diamines. Investigations with the N4-Troc form of these heterocycles have led to manifold improvements in reaction performance and scope and have revealed unique differences in the stability and reactivity of such compounds dictated by the choice of N4-protecting group.

SUBMITTER: Olson DE

PROVIDER: S-EPMC3123413 | biostudies-literature | 2011 Jul

REPOSITORIES: biostudies-literature

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Synthesis and reactivity of unique heterocyclic structures en route to substituted diamines.

Olson David E DE Maruniak Autumn A Malhotra Sushant S Trost Barry M BM Du Bois J J

Organic letters 20110527 13

Rhodium-catalyzed oxidative cyclization of allylic hydroxylamine-derived sulfamate esters furnishes a novel family of bicyclic aziridines that serve as functional precursors to substituted diamines. Investigations with the N4-Troc form of these heterocycles have led to manifold improvements in reaction performance and scope and have revealed unique differences in the stability and reactivity of such compounds dictated by the choice of N4-protecting group. ...[more]

PMID: 21618989

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