Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage

Wenguo Yang; Davin Tan; Richmond Lee; Lixin Li; Yuanhang Pan; Kuo-Wei Huang; Choonhong Tan; Zhiyong Jiang

doi:10.1002/asia.201100863

Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage

Wenguo Yang, Davin Tan, Richmond Lee, Lixin Li, Yuanhang Pan, Kuo-Wei Huang, Choonhong Tan, Zhiyong Jiang

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

5 Scopus citations

Abstract

Through the cleavage of the C-C bond, the first catalytic tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts has been presented. Various S N2′-like C-, S-, and P-allylic compounds could be obtained with exclusive E configuration in good to excellent yields. The Michael product could also be easily prepared by tuning the β-C-substituent group of the α-methylene ester under the same reaction conditions. Calculated relative energies of various transition states by DFT methods strongly support the observed chemoselectivity and diastereoselectivity. © 2012 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.

Original language	English (US)
Pages (from-to)	771-777
Number of pages	7
Journal	Chemistry - An Asian Journal
Volume	7
Issue number	4
DOIs	https://doi.org/10.1002/asia.201100863
State	Published - Feb 8 2012

Bibliographical 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), Specialized Research Fund for the Doctoral Program of Higher Education (20104103120002) to Z.J., International Cooperation Foundation of Henan Province (104300510062) to Z.J. and C. H. T. and KAUST (4000000076) to K.-W. H. are greatly appreciated.

ASJC Scopus subject areas

General Chemistry

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title = "Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage",

abstract = "Through the cleavage of the C-C bond, the first catalytic tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts has been presented. Various S N2′-like C-, S-, and P-allylic compounds could be obtained with exclusive E configuration in good to excellent yields. The Michael product could also be easily prepared by tuning the β-C-substituent group of the α-methylene ester under the same reaction conditions. Calculated relative energies of various transition states by DFT methods strongly support the observed chemoselectivity and diastereoselectivity. {\textcopyright} 2012 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.",

author = "Wenguo Yang and Davin Tan and Richmond Lee and Lixin Li and Yuanhang Pan 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), Specialized Research Fund for the Doctoral Program of Higher Education (20104103120002) to Z.J., International Cooperation Foundation of Henan Province (104300510062) to Z.J. and C. H. T. and KAUST (4000000076) to K.-W. H. are greatly appreciated.",

year = "2012",

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doi = "10.1002/asia.201100863",

language = "English (US)",

volume = "7",

pages = "771--777",

journal = "Chemistry - An Asian Journal",

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T1 - Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage

AU - Yang, Wenguo

AU - Tan, Davin

AU - Lee, Richmond

AU - Li, Lixin

AU - Pan, Yuanhang

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), Specialized Research Fund for the Doctoral Program of Higher Education (20104103120002) to Z.J., International Cooperation Foundation of Henan Province (104300510062) to Z.J. and C. H. T. and KAUST (4000000076) to K.-W. H. are greatly appreciated.

PY - 2012/2/8

Y1 - 2012/2/8

N2 - Through the cleavage of the C-C bond, the first catalytic tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts has been presented. Various S N2′-like C-, S-, and P-allylic compounds could be obtained with exclusive E configuration in good to excellent yields. The Michael product could also be easily prepared by tuning the β-C-substituent group of the α-methylene ester under the same reaction conditions. Calculated relative energies of various transition states by DFT methods strongly support the observed chemoselectivity and diastereoselectivity. © 2012 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.

AB - Through the cleavage of the C-C bond, the first catalytic tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts has been presented. Various S N2′-like C-, S-, and P-allylic compounds could be obtained with exclusive E configuration in good to excellent yields. The Michael product could also be easily prepared by tuning the β-C-substituent group of the α-methylene ester under the same reaction conditions. Calculated relative energies of various transition states by DFT methods strongly support the observed chemoselectivity and diastereoselectivity. © 2012 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.

UR - http://hdl.handle.net/10754/562090

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DO - 10.1002/asia.201100863

M3 - Article

C2 - 22318922

SN - 1861-4728

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SP - 771

EP - 777

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 4

ER -

Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage

Abstract

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