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Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones.
J Org Chem. 2013 May 17; 78(10):5067-72.JO

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Tong G
Institute of Chemical Biology, Henan University, Kaifeng, Henan, 475004, PR China.
Zhu B
No affiliation info available
Lee R
No affiliation info available
Yang W
No affiliation info available
Tan D
No affiliation info available
Yang C
No affiliation info available
Han Z
No affiliation info available
Yan L
No affiliation info available
Huang KW
No affiliation info available
Jiang Z
No affiliation info available

MeSH

AlkylationAllyl CompoundsCarbonatesKetonesMolecular StructureStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23594149

Citation

Tong, Guanghu, et al. "Highly Enantio- and Diastereoselective Allylic Alkylation of Morita-Baylis-Hillman Carbonates With Allyl Ketones." The Journal of Organic Chemistry, vol. 78, no. 10, 2013, pp. 5067-72.
Tong G, Zhu B, Lee R, et al. Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones. J Org Chem. 2013;78(10):5067-72.
Tong, G., Zhu, B., Lee, R., Yang, W., Tan, D., Yang, C., Han, Z., Yan, L., Huang, K. W., & Jiang, Z. (2013). Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones. The Journal of Organic Chemistry, 78(10), 5067-72. https://doi.org/10.1021/jo400496z
Tong G, et al. Highly Enantio- and Diastereoselective Allylic Alkylation of Morita-Baylis-Hillman Carbonates With Allyl Ketones. J Org Chem. 2013 May 17;78(10):5067-72. PubMed PMID: 23594149.
* Article titles in AMA citation format should be in sentence-case
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, Y1 - 2013/04/26/ PY - 2013/4/19/entrez PY - 2013/4/19/pubmed PY - 2013/11/6/medline SP - 5067 EP - 72 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 10 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. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23594149/Highly_enantio__and_diastereoselective_allylic_alkylation_of_Morita_Baylis_Hillman_carbonates_with_allyl_ketones_ L2 - https://doi.org/10.1021/jo400496z DB - PRIME DP - Unbound Medicine ER -