Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates

Wenguo Yang; Davin Tan; Lixin Li; Zhiqiang Han; Lin Yan; Kuo-Wei Huang; Choonhong Tan; Zhiyong Jiang

doi:10.1021/jo3012539

Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates

Wenguo Yang, Davin Tan, Lixin Li, Zhiqiang Han, Lin Yan, Kuo-Wei Huang, Choonhong Tan, Zhiyong Jiang

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

The asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity. © 2012 American Chemical Society.

Original language	English (US)
Pages (from-to)	6600-6607
Number of pages	8
Journal	The Journal of Organic Chemistry
Volume	77
Issue number	15
DOIs	https://doi.org/10.1021/jo3012539
State	Published - Jul 26 2012

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo3012539

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@article{2201285a20c34e5085994fe1913d07a7,

title = "Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates",

abstract = "The asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity. {\textcopyright} 2012 American Chemical Society.",

author = "Wenguo Yang and Davin Tan and Lixin Li and Zhiqiang Han and Lin Yan and Kuo-Wei Huang and Choonhong Tan and Zhiyong Jiang",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Financial support from the National Natural Science Foundation of China (21072044), Excellent Youth Foundation of Henan Scientific Committee (114100510003), and the Program for New Century Excellent Talents in University of Ministry of Education (NCET-11-0938) is greatly appreciated. We also thank Professor Hongwei Zhou (Zhejiang University) and Professor Fuwei Li (Lanzhou Institute of Chemical Physics) for their generous help in high resolution mass spectrum analysis.",

year = "2012",

month = jul,

day = "26",

doi = "10.1021/jo3012539",

language = "English (US)",

volume = "77",

pages = "6600--6607",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "15",

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TY - JOUR

T1 - Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates

AU - Yang, Wenguo

AU - Tan, Davin

AU - Li, Lixin

AU - Han, Zhiqiang

AU - Yan, Lin

AU - Huang, Kuo-Wei

AU - Tan, Choonhong

AU - Jiang, Zhiyong

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Financial support from the National Natural Science Foundation of China (21072044), Excellent Youth Foundation of Henan Scientific Committee (114100510003), and the Program for New Century Excellent Talents in University of Ministry of Education (NCET-11-0938) is greatly appreciated. We also thank Professor Hongwei Zhou (Zhejiang University) and Professor Fuwei Li (Lanzhou Institute of Chemical Physics) for their generous help in high resolution mass spectrum analysis.

PY - 2012/7/26

Y1 - 2012/7/26

N2 - The asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity. © 2012 American Chemical Society.

AB - The asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity. © 2012 American Chemical Society.

UR - http://hdl.handle.net/10754/562269

UR - https://pubs.acs.org/doi/10.1021/jo3012539

UR - http://www.scopus.com/inward/record.url?scp=84864585863&partnerID=8YFLogxK

U2 - 10.1021/jo3012539

DO - 10.1021/jo3012539

M3 - Article

C2 - 22816444

SN - 0022-3263

VL - 77

SP - 6600

EP - 6607

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 15

ER -

Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates

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CCDC 874217: Experimental Crystal Structure Determination : Methyl 3-(4-bromophenyl)-5-((1-(4-bromophenyl)-4-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)(phenyl)methyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

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Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates

Abstract

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CCDC 874217: Experimental Crystal Structure Determination : Methyl 3-(4-bromophenyl)-5-((1-(4-bromophenyl)-4-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)(phenyl)methyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

Cite this