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A novel synthesis of optically active α-arylamino ketones through an organocatalytic enantioselective Amadori-Heyns rearrangement is described.

This concept review describes the recent achievements on the Heyns rearrangement appeared in literature over the last decade and aims to provide the reader with a general overview of the fundamental synthetic advances in this research area. [ABSTRACT FROM AUTHOR]

An organocatalytic enantioselective synthesis of α-(benzylamino)cyclobutanones has been achieved by employing a tandem condensation/intramolecular rearrangement/proton transfer reaction and starting from racemic α-hydroxycyclobutanone and a selection of benzylamines. This reaction sequence afforded the products in good to high yields with moderate to high enantioselectivities. [ABSTRACT FROM AUTHOR]

A practical method for the synthesis of optically active α-amino cyclobutanones has been developed, via an organocatalytic asymmetric condensation reaction between racemic 2-hydroxycyclobutanone and chiral N-alkyl-α-amino acid ester derivatives. [ABSTRACT FROM AUTHOR]

A catalytic enantioselective synthesis of α-arylaminocyclobutanones from racemic α-hydroxycyclobutanone and a selection of N-alkylanilines has been established, via a tandem condensation/keto-enol tautomerization process reminiscent of the Amadori and Heyns rearrangements. [ABSTRACT FROM AUTHOR]

A simple and practical protocol for the construction of synthetically important quaternary α-benzyl- and α-allyl-α-methylamino cyclobutanones in good to high yield, via a sequential one-pot methylation/sigmatropic rearrangement, has been accomplished for the first time. The quaternary α-alkyl-α-amino cyclobutanones could be further manipulated, affording synthetically interesting scaffolds such as highly substituted tryptamines and cyclobuta-fused indolines. [ABSTRACT FROM AUTHOR]

An asymmetric synthesis of α-aryl amino-β-nitro cyclohexanes has been achieved by means of a tandem aza-Michael addition-protonation reaction starting from 1-nitro cyclohexene and anilines. The transformation is proposed to proceed via a transient nitrile enolate which is subsequently stereoselectively protonated by an intramolecular transfer of the proton from nitrogen to the nitronate α-carbon. [ABSTRACT FROM AUTHOR]

via tandem condensation/intramolecular rearrangement/proton transfer reaction of hydroxycyclobutanone and various secondary amines [ABSTRACT FROM AUTHOR]