Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids

Razvan C. Cioc; Veronica Estevez; Daan J. van der Niet; Christophe M. L. Vande Velde; Nikolaus G. Turrini; Melanie Hall; Kurt Faber; Eelco Ruijter; Romano V. A. Orru

doi:10.1002/ejoc.201601432

Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids

Razvan C. Cioc, Veronica Estevez, Daan J. van der Niet, Christophe M. L. Vande Velde, Nikolaus G. Turrini, Melanie Hall, Kurt Faber, Eelco Ruijter, Romano V. A. Orru

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

Abstract

We report the use of bifunctional starting materials (ketoacids) in a diastereoselective Passerini three-center-two-component reaction. Study of the reaction scope revealed the required structural features for stereoselectivity in the isocyanide addition. In this system, an interesting isomerization of the primary Passerini product – the α-carboxamido lactone – into an atypical product, an α-hydroxy imide, was found to occur under acidic conditions. Furthermore, enantioenriched Passerini products can be generated from an enantioenriched ketoacid obtained by chemoenzymatic synthesis.

Original language	English
Pages (from-to)	1262-1271
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	9
DOIs	https://doi.org/10.1002/ejoc.201601432
Publication status	Published - 3 Mar 2017

Funding

Funders	Funder number
Seventh Framework Programme	115360

Keywords

Cyclization
Diastereoselectivity
Ketoacids
Lactones
Multicomponent reactions
Rearrangement

UN SDGs

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

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10.1002/ejoc.201601432

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Cioc, R. C., Estevez, V., van der Niet, D. J., Vande Velde, C. M. L., Turrini, N. G., Hall, M., Faber, K., Ruijter, E., & Orru, R. V. A. (2017). Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids. European Journal of Organic Chemistry, 2017(9), 1262-1271. https://doi.org/10.1002/ejoc.201601432

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title = "Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids",

abstract = "We report the use of bifunctional starting materials (ketoacids) in a diastereoselective Passerini three-center-two-component reaction. Study of the reaction scope revealed the required structural features for stereoselectivity in the isocyanide addition. In this system, an interesting isomerization of the primary Passerini product – the α-carboxamido lactone – into an atypical product, an α-hydroxy imide, was found to occur under acidic conditions. Furthermore, enantioenriched Passerini products can be generated from an enantioenriched ketoacid obtained by chemoenzymatic synthesis.",

keywords = "Cyclization, Diastereoselectivity, Ketoacids, Lactones, Multicomponent reactions, Rearrangement",

author = "Cioc, {Razvan C.} and Veronica Estevez and {van der Niet}, {Daan J.} and {Vande Velde}, {Christophe M. L.} and Turrini, {Nikolaus G.} and Melanie Hall and Kurt Faber and Eelco Ruijter and Orru, {Romano V. A.}",

year = "2017",

month = mar,

day = "3",

doi = "10.1002/ejoc.201601432",

language = "English",

volume = "2017",

pages = "1262--1271",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "9",

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T1 - Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids

AU - Cioc, Razvan C.

AU - Estevez, Veronica

AU - van der Niet, Daan J.

AU - Vande Velde, Christophe M. L.

AU - Turrini, Nikolaus G.

AU - Hall, Melanie

AU - Faber, Kurt

AU - Ruijter, Eelco

AU - Orru, Romano V. A.

PY - 2017/3/3

Y1 - 2017/3/3

N2 - We report the use of bifunctional starting materials (ketoacids) in a diastereoselective Passerini three-center-two-component reaction. Study of the reaction scope revealed the required structural features for stereoselectivity in the isocyanide addition. In this system, an interesting isomerization of the primary Passerini product – the α-carboxamido lactone – into an atypical product, an α-hydroxy imide, was found to occur under acidic conditions. Furthermore, enantioenriched Passerini products can be generated from an enantioenriched ketoacid obtained by chemoenzymatic synthesis.

AB - We report the use of bifunctional starting materials (ketoacids) in a diastereoselective Passerini three-center-two-component reaction. Study of the reaction scope revealed the required structural features for stereoselectivity in the isocyanide addition. In this system, an interesting isomerization of the primary Passerini product – the α-carboxamido lactone – into an atypical product, an α-hydroxy imide, was found to occur under acidic conditions. Furthermore, enantioenriched Passerini products can be generated from an enantioenriched ketoacid obtained by chemoenzymatic synthesis.

KW - Cyclization

KW - Diastereoselectivity

KW - Ketoacids

KW - Lactones

KW - Multicomponent reactions

KW - Rearrangement

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U2 - 10.1002/ejoc.201601432

DO - 10.1002/ejoc.201601432

M3 - Article

SN - 1434-193X

VL - 2017

SP - 1262

EP - 1271

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 9

ER -

Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids

Abstract

Funding

Keywords

UN SDGs

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Persistent URL (handle)

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CCDC 1511110: Experimental Crystal Structure Determination

CCDC 1511111: Experimental Crystal Structure Determination

Cite this

Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids

Abstract

Funding

Keywords

UN SDGs

Access to Document

Persistent URL (handle)

Other files and links

Fingerprint

Datasets

CCDC 1511110: Experimental Crystal Structure Determination

CCDC 1511111: Experimental Crystal Structure Determination

Cite this