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

John Braun; Maxim I. Ariëns; Bianca T. Matsuo; Steven De Vries; Ellen D.H. Van Wordragen; Brecht D. Ellenbroek; Christophe M.L. Vande Velde; Romano V.A. Orru; Eelco Ruijter

doi:10.1021/acs.orglett.8b02232

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

John Braun, Maxim I. Ariëns, Bianca T. Matsuo, Steven De Vries, Ellen D.H. Van Wordragen, Brecht D. Ellenbroek, Christophe M.L. Vande Velde, Romano V.A. Orru, Eelco Ruijter^*

^*Corresponding author for this work

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

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.

Original language	English
Pages (from-to)	6611-6615
Number of pages	5
Journal	Organic letters
Volume	20
Issue number	21
Early online date	12 Oct 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b02232
Publication status	Published - 2 Nov 2018

Funding

The Netherlands Organization of Scientific Research (NWO) is acknowledged for financial support. B.T.M. acknowledges the Brazilian Federal Agency for Support and Evaluation of Graduate Education within the Ministry of Education of Brazil (CAPES) for a MSc scholarship. We thank Jordy Saya, Jurrien Collet and Gydo van der Heijden (all VU Amsterdam) for their valuable input in many fruitful discussions. Mustafa Hashemie (experimental contribution), Elwin Janssen (NMR maintenance), Daniel̈ Preschel and Jurrien Collet (HRMS measurements) are acknowledged for their technical assistance (all VU Amsterdam). We thank Prof. Kristof Van Hecke (University of Gent) for measuring time on the diffractometer, for which funding through the Hercules Foundation (Project AUGE/11/029 “3D-SPACE: 3D Structural Platform Aiming for Chemical Excellence”) is acknowledged.

Funders	Funder number
Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
Nederlandse Organisatie voor Wetenschappelijk Onderzoek

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acs.orglett.8b02232

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title = "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 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.",

author = "John Braun and Ari{\"e}ns, {Maxim I.} and Matsuo, {Bianca T.} and {De Vries}, Steven and {Van Wordragen}, {Ellen D.H.} and Ellenbroek, {Brecht D.} and {Vande Velde}, {Christophe M.L.} and Orru, {Romano V.A.} and Eelco Ruijter",

year = "2018",

month = nov,

day = "2",

doi = "10.1021/acs.orglett.8b02232",

language = "English",

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T1 - Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji-Trost Cascade Cyclization

AU - Braun, John

AU - Ariëns, Maxim I.

AU - Matsuo, Bianca T.

AU - De Vries, Steven

AU - Van Wordragen, Ellen D.H.

AU - Ellenbroek, Brecht D.

AU - Vande Velde, Christophe M.L.

AU - Orru, Romano V.A.

AU - Ruijter, Eelco

PY - 2018/11/2

Y1 - 2018/11/2

N2 - 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.

AB - 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.

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

Abstract

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UN SDGs

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CCDC 1856030: Experimental Crystal Structure Determination

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

Abstract

Funding

UN SDGs

Access to Document

Persistent URL (handle)

Other files and links

Fingerprint

Datasets

CCDC 1856030: Experimental Crystal Structure Determination

Cite this