Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones

Guanghu Tong; Bo Zhu; Richmond Lee; Wenguo Yang; Davin Tan; Caiyun Yang; Zhiqiang Han; Lin Yan; Kuo-Wei Huang; Zhiyong Jiang

doi:10.1021/jo400496z

Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones

Guanghu Tong, Bo Zhu, Richmond Lee, Wenguo Yang, Davin Tan, Caiyun Yang, Zhiqiang Han, Lin Yan, Kuo-Wei Huang, Zhiyong Jiang

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

30 Scopus citations

Abstract

The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared. © 2013 American Chemical Society.

Original language	English (US)
Pages (from-to)	5067-5072
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	78
Issue number	10
DOIs	https://doi.org/10.1021/jo400496z
State	Published - Apr 26 2013

ASJC Scopus subject areas

Organic Chemistry

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CCDC 909467: Experimental Crystal Structure Determination : Methyl 2-methylene-3-phenyl-4-(2-thienylcarbonyl)hex-5-enoate
Tong, G. (Creator), Zhu, B. (Creator), Lee, R. (Creator), Yang, W. (Creator), Tan, D. (Creator), Yang, C. (Creator), Han, Z. (Creator), Yan, L. (Creator), Huang, K. (Creator), Jiang, Z. (Creator), Tong, G. (Creator), Zhu, B. (Creator), Yang, W. (Creator), Yang, C. (Creator), Han, Z. (Creator), Yan, L. (Creator) & Jiang, Z. (Creator), Cambridge Crystallographic Data Centre, Mar 28 2014
DOI: 10.5517/cczjcnh, http://hdl.handle.net/10754/624757
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@article{be3645cae71549eeaf6e473b9bbb6e76,

title = "Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones",

abstract = "The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared. {\textcopyright} 2013 American Chemical Society.",

author = "Guanghu Tong and Bo Zhu and Richmond Lee and Wenguo Yang and Davin Tan and Caiyun Yang and Zhiqiang Han and Lin Yan and Kuo-Wei Huang and Zhiyong Jiang",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Financial support from the National Natural Science Foundation of China (No. 21072044, 21202034), the Program for New Century Excellent Talents in University of Ministry of Education (NCET-11-0938), Excellent Youth Foundation of Henan Scientific Committee (114100510003) and Specialized Research Fund for the Doctoral Program of Higher Education (20104103120002) are greatly appreciated. We also thank Professor Choon-Hong Tan (Nanyang Technological University, Singapore) and Professor Fuwei Li (Lanzhou Institute of Chemical Physics, PR China) for their generous help in high resolution mass spectrum analysis.",

year = "2013",

month = apr,

day = "26",

doi = "10.1021/jo400496z",

language = "English (US)",

volume = "78",

pages = "5067--5072",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "10",

}

Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones. / Tong, Guanghu; Zhu, Bo; Lee, Richmond; Yang, Wenguo; Tan, Davin; Yang, Caiyun; Han, Zhiqiang; Yan, Lin; Huang, Kuo-Wei; Jiang, Zhiyong.

In: Journal of Organic Chemistry, Vol. 78, No. 10, 26.04.2013, p. 5067-5072.

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

TY - JOUR

T1 - Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones

AU - Tong, Guanghu

AU - Zhu, Bo

AU - Lee, Richmond

AU - Yang, Wenguo

AU - Tan, Davin

AU - Yang, Caiyun

AU - Han, Zhiqiang

AU - Yan, Lin

AU - Huang, Kuo-Wei

AU - Jiang, Zhiyong

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Financial support from the National Natural Science Foundation of China (No. 21072044, 21202034), the Program for New Century Excellent Talents in University of Ministry of Education (NCET-11-0938), Excellent Youth Foundation of Henan Scientific Committee (114100510003) and Specialized Research Fund for the Doctoral Program of Higher Education (20104103120002) are greatly appreciated. We also thank Professor Choon-Hong Tan (Nanyang Technological University, Singapore) and Professor Fuwei Li (Lanzhou Institute of Chemical Physics, PR China) for their generous help in high resolution mass spectrum analysis.

PY - 2013/4/26

Y1 - 2013/4/26

N2 - The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared. © 2013 American Chemical Society.

AB - The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared. © 2013 American Chemical Society.

UR - http://hdl.handle.net/10754/562767

UR - https://pubs.acs.org/doi/10.1021/jo400496z

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VL - 78

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 10

ER -

Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones

Abstract

ASJC Scopus subject areas

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CCDC 909467: Experimental Crystal Structure Determination : Methyl 2-methylene-3-phenyl-4-(2-thienylcarbonyl)hex-5-enoate

Cite this