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Catalytic Asymmetric Cascade Cyclization for Constructing Three Contiguous Stereocenters in Pyrrolobenzodiazepine-Based Cyclopentanones.

08:00 EDT 1st April 2019 | BioPortfolio

Summary of "Catalytic Asymmetric Cascade Cyclization for Constructing Three Contiguous Stereocenters in Pyrrolobenzodiazepine-Based Cyclopentanones."

A chiral Brønsted acid catalyzed highly enantio- and diastereoselective cascade cyclization has been developed to streamline the synthesis of valuable multifunctionalized enantioenriched cyclopenta[ f]pyrrolo[1,2- d][1,4]diazepinones bearing three contiguous stereocenters in high yields with excellent control of stereochemistry from a wide range of both readily available 2-furylcarbinols and (1 H-pyrrol-1-yl)anilines, which represents the first asymmetric intramolecular conjugate addition of α,β-unsaturated cycloketones with inert N-substituted pyrroles as well as the first enantioselective aza-piancatelli rearrangement/Friedel-Crafts alkylation cascade reaction.

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Name: Organic letters
ISSN: 1523-7052
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An amino acid formed by cyclization of leucine. It has cytostatic, immunosuppressive and antineoplastic activities.

Compounds with three contiguous nitrogen atoms in linear format, H2N-N=NH, and hydrocarbyl derivatives.

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