2-Butenylene dicarbamate

An interesting intramolecular variation of this reaction provides oxazolidones, which may be hydrolyzed to synthetically useful optically active 2-amino-3-butenols (eq 8). The absolute stereochemistry of the stereocenter formed is dependent upon the geometry about the double bond of the 2-butenylene dicarbamate substrate. A related Pd -promoted [3 + 2] cycloaddition of an activated alkene with a 2-(sulfonylmethyl)-2-propenyl carbonate, using the bis(hydroxyalkyl)-substituted ligand (8), gave methylenecyclopentane derivatives with high asymmetric induction. ... 

Intramolecular asymmetric allylic substitution reactions have been applied to the synthesis of optically active cyclic compounds. The high efficiency of the dihydroxylated ferrocenylphosphine 8b has been shown in the cyclization of 2-butenylene dicarbamates 52 to form optically active 4-vinyl-2-oxazolidones 53, which are... 

The palladium-catalyzed intramolecular addition of N—H to 2-butenylene dicarbamates leads to cyclization. Optical activity can be induced by chiral fer-rocenylphosphines carrying amino substituents with hydroxyalkyl side-chains such as (45). The reaction proceeds via 7r-allyl palladium complexes. The primary product can be hydrolyzed to give optically active aminoalcohols (Scheme... 

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