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

39 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

Access to Document

10.1021/jo400496z

Cite this

@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",

}

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

UR - http://www.scopus.com/inward/record.url?scp=84878092049&partnerID=8YFLogxK

U2 - 10.1021/jo400496z

DO - 10.1021/jo400496z

M3 - Article

C2 - 23594149

SN - 0022-3263

VL - 78

SP - 5067

EP - 5072

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 10

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

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

Cite this

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

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

Cite this