engleski

Synthesis of novel guanidinium- substituted oxanorbornanes and their cocatalytic activity in aldol reaction

Norbornane structures and their oxa-derivatives have rigid scaffold and are good mimics of secondary structures in polypeptides such as β-turn and β-hairpin. Norbornane motifs can serve as the inducers of well-defined hydrogen bonding patterns in peptides [1]. Hydrogen bond plays a crucial role in enzymes and small molecule organocatalysis. Thioureas and guanidines are two types of such organocatalysts [2, 3]. Aldol reactions catalysed with L-proline are known to show poor diastereoselectivity in formation of anti and syn adducts and can be improved by adding guanidinium salts or thioureas as cocatalysts [4, 5]. Herein we report a synthetic route to a novel thiourea and guanidinium oxanorbornanes carrying different structural motifs (figure 1) and their activity in L-proline catalyzed aldol reaction.

Oxanorbornanes ; Guanidine ; Cocatalytic activity

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