Synthesis and diastereoselective reactions of N,N-dibenzylamino aldehydes and related compounds

Article Abstract:

Studies have been conducted on the synthesis and reactions of a new class of alpha-amino aldehydes, the N,N-dibenzylamino aldehydes. These building blocks can be prepared from alpha-amino acids or from other chiral sources. Findings indicate that the presence of two protective benzyl groups is of crucial importance in influencing the direction and degree of diastereoselectivity. Further investigations have been done regarding the reactions of related N,N-dibenzylamino ketones, aldimines, and alpha,beta-unsaturated esters.

Benzene, Reactivity (Chemistry), Esters, Amino compounds, Aldehydes, Ketones

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Substrate-directable chemical reactions

Article Abstract:

The different heteroatom-directed organic reactions, specifically those which involve transient interaction of a substrate functional group with the incoming reagents are discussed and analyzed. The reduced degrees of freedom due to the heteroatom association with the reagents makes the reactions capable of hosting systems which are highly stereoselective. The internal- heteroatom-influenced transition-metal catalyzed reaction may reach regio- and stereoselectivity levels often attained by natural enzymes.

Hydrogenation

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Asymmetric ylide reactions: epoxidation, cyclopropanation, aziridination, olefination, and rearrangement

Article Abstract:

Aziridination, cyclopropanation, epoxidation, olefination and rearrangement are asymmetric ylide reactions. Previous studies have demonstrated such reactions on heteroatom ylides O, S, Se, P, N and As and their derivatives. Further studies, however, are needed before the potential of the asymmetric ylide approach is truly realized in synthesis. Research should focus on catalytic asymmetric processes and carbonyl compound dynamic kinetic resolution.

Organic compounds, Chemical tests and reagents, Reagents

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