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Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water.
J Org Chem. 2011 Aug 19; 76(16):6894-900.JO

Abstract

A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using (18)O-labeling experiments.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhu B
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan 475004, People's Republic of China.
Yan L
No affiliation info available
Pan Y
No affiliation info available
Lee R
No affiliation info available
Liu H
No affiliation info available
Han Z
No affiliation info available
Huang KW
No affiliation info available
Tan CH
No affiliation info available
Jiang Z
No affiliation info available

MeSH

AlcoholsCarbonatesCatalysisHydroxylationLewis BasesMolecular StructureStereoisomerismWater

Pub Type(s)

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

Language

eng

PubMed ID

21751799

Citation

Zhu, Bo, et al. "Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita-Baylis-Hillman Carbonates With Water." The Journal of Organic Chemistry, vol. 76, no. 16, 2011, pp. 6894-900.
Zhu B, Yan L, Pan Y, et al. Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water. J Org Chem. 2011;76(16):6894-900.
Zhu, B., Yan, L., Pan, Y., Lee, R., Liu, H., Han, Z., Huang, K. W., Tan, C. H., & Jiang, Z. (2011). Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water. The Journal of Organic Chemistry, 76(16), 6894-900. https://doi.org/10.1021/jo201096e
Zhu B, et al. Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita-Baylis-Hillman Carbonates With Water. J Org Chem. 2011 Aug 19;76(16):6894-900. PubMed PMID: 21751799.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water. AU - Zhu,Bo, AU - Yan,Lin, AU - Pan,Yuanhang, AU - Lee,Richmond, AU - Liu,Hongjun, AU - Han,Zhiqiang, AU - Huang,Kuo-Wei, AU - Tan,Choon-Hong, AU - Jiang,Zhiyong, Y1 - 2011/07/22/ PY - 2011/7/15/entrez PY - 2011/7/15/pubmed PY - 2011/12/17/medline SP - 6894 EP - 900 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 16 N2 - A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using (18)O-labeling experiments. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21751799/Lewis_base_catalyzed_enantioselective_allylic_hydroxylation_of_Morita_Baylis_Hillman_carbonates_with_water_ L2 - https://doi.org/10.1021/jo201096e DB - PRIME DP - Unbound Medicine ER -