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

Research output: Contribution to JournalArticleAcademicpeer-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 languageEnglish
Pages (from-to)6611-6615
JournalOrganic Letters
Volume20
Issue number21
Early online date12 Oct 2018
DOIs
Publication statusPublished - 2 Nov 2018

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Lactams
Nucleophiles
Chirality
nucleophiles
Cyclization
carbohydrates
chirality
cascades
Carbon
Carbohydrates
carbon
rings
synthesis
products

Cite this

Braun, John ; Ariëns, Maxim I. ; Matsuo, Bianca T. ; De Vries, Steven ; Van Wordragen, Ellen D.H. ; Ellenbroek, Brecht D. ; Vande Velde, Christophe M.L. ; Orru, Romano V.A. ; Ruijter, Eelco. / Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji-Trost Cascade Cyclization. In: Organic Letters. 2018 ; Vol. 20, No. 21. pp. 6611-6615.
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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",
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Braun, J, Ariëns, MI, Matsuo, BT, De Vries, S, Van Wordragen, EDH, Ellenbroek, BD, Vande Velde, CML, Orru, RVA & Ruijter, E 2018, 'Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji-Trost Cascade Cyclization' Organic Letters, vol. 20, no. 21, pp. 6611-6615. https://doi.org/10.1021/acs.orglett.8b02232

Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji-Trost Cascade Cyclization. / Braun, John; Ariëns, Maxim I.; Matsuo, Bianca T.; De Vries, Steven; Van Wordragen, Ellen D.H.; Ellenbroek, Brecht D.; Vande Velde, Christophe M.L.; Orru, Romano V.A.; Ruijter, Eelco.

In: Organic Letters, Vol. 20, No. 21, 02.11.2018, p. 6611-6615.

Research output: Contribution to JournalArticleAcademicpeer-review

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AU - Van Wordragen, Ellen D.H.

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AU - Ruijter, Eelco

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