Asymmetric synthesis of highly substituted azapolycyclic compounds via 2-alkenyl sulfoximines: potential scaffolds for peptide mimetics
M Reggelin, B Junker, T Heinrich…
Index: Reggelin, Michael; Junker, Bernd; Heinrich, Timo; Slavik, Stefan; Buehle, Philipp Journal of the American Chemical Society, 2006 , vol. 128, # 12 p. 4023 - 4034
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Citation Number: 29
Abstract
The application of metalated, enantiomerically pure acyclic and cyclic 2-alkenyl sulfoximines for the synthesis of highly substituted aza (poly) cyclic ring systems is described. The method relies on a one-pot combination of a reagent-controlled allyl transfer reaction to α-or β-amino aldehydes, followed by a Michael-type cyclization of the intermediate vinyl sulfoximines generated in the first step. The sulfur-free target compounds are preferentially obtained by ...
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