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Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji-Trost Cascade Cyclization.

ABSTRACT: A stereoselective intramolecular Tsuji-Trost cascade cyclization of (homo)allylic vicinal diacetates with a pendant ?-ketoamide or related carbon nucleophile to give ?-lactam-fused vinylcyclopropanes is reported. In addition to two new rings, the products contain three new C-C stereocenters (two of which are quaternary) with a 9:1 dr. Moreover, the reaction proceeds in >94% enantiospecificity with optically enriched starting materials, using an inexpensive carbohydrate as the source of chirality.

SUBMITTER: Braun J 

PROVIDER: S-EPMC6218879 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji-Trost Cascade Cyclization.

Braun John J   Ariëns Maxim I MI   Matsuo Bianca T BT   de Vries Steven S   van Wordragen Ellen D H EDH   Ellenbroek Brecht D BD   Vande Velde Christophe M L CML   Orru Romano V A RVA   Ruijter Eelco E  

Organic letters 20181012 21

A stereoselective intramolecular Tsuji-Trost cascade cyclization of (homo)allylic vicinal diacetates with a pendant β-ketoamide or related carbon nucleophile to give γ-lactam-fused vinylcyclopropanes is reported. In addition to two new rings, the products contain three new C-C stereocenters (two of which are quaternary) with a 9:1 dr. Moreover, the reaction proceeds in >94% enantiospecificity with optically enriched starting materials, using an inexpensive carbohydrate as the source of chirality  ...[more]

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