Morita-Baylis-Hillman (MBH) Reaction Derived Nitroallylic Alcohols, Acetates and Amines as Synthons in Organocatalysis and Heterocycle Synthesis.
Chem Rec. 2017 Mar; 17(3):363-381.CR

Abstract

The Morita-Baylis-Hillman (MBH) reaction is one of the most useful and efficient protocols for constructing new carbon-carbon bonds between an activated olefin and electrophiles in the presence of a tertiary amine/phosphine. Herein, we present the use of MBH alcohols, which are obtained from the reaction of nitrostyrenes with aldehydes, as well as acetates and amines derived thereof in several organocatalytic transformations. Densely functionalised MBH adducts can also be used to synthesise substituted heteroaromatic compounds, such as furan, pyrrole, pyrazole and imidazole derivatives.

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Authors+Show Affiliations

Huang WY

Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan, 116 (ROC).

Anwar S

Division of Chemistry, Department of Science and Humanities, Vignan's Foundation for Science, Technology and Research University-VFSTRU, (Vignan University) Vadlamudi, Guntur 522 213, Andhra Pradesh, India.

Chen K

Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan, 116 (ROC).

Pub Type(s)

Journal Article

Review

Language

eng

PubMed ID

27701816

Citation

Huang, Wan-Yun, et al. "Morita-Baylis-Hillman (MBH) Reaction Derived Nitroallylic Alcohols, Acetates and Amines as Synthons in Organocatalysis and Heterocycle Synthesis." Chemical Record (New York, N.Y.), vol. 17, no. 3, 2017, pp. 363-381.

Huang WY, Anwar S, Chen K. Morita-Baylis-Hillman (MBH) Reaction Derived Nitroallylic Alcohols, Acetates and Amines as Synthons in Organocatalysis and Heterocycle Synthesis. Chem Rec. 2017;17(3):363-381.

Huang, W. Y., Anwar, S., & Chen, K. (2017). Morita-Baylis-Hillman (MBH) Reaction Derived Nitroallylic Alcohols, Acetates and Amines as Synthons in Organocatalysis and Heterocycle Synthesis. Chemical Record (New York, N.Y.), 17(3), 363-381. https://doi.org/10.1002/tcr.201600075

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Morita-Baylis-Hillman (MBH) Reaction Derived Nitroallylic Alcohols, Acetates and Amines as Synthons in Organocatalysis and Heterocycle Synthesis. AU - Huang,Wan-Yun, AU - Anwar,Shaik, AU - Chen,Kwunmin, Y1 - 2016/10/04/ PY - 2016/04/14/received PY - 2016/10/5/pubmed PY - 2016/10/5/medline PY - 2016/10/5/entrez KW - asymmetric synthesis KW - heterocycles KW - nitroallylic alcohols KW - organocatalysis KW - sequential reaction SP - 363 EP - 381 JF - Chemical record (New York, N.Y.) JO - Chem Rec VL - 17 IS - 3 N2 - The Morita-Baylis-Hillman (MBH) reaction is one of the most useful and efficient protocols for constructing new carbon-carbon bonds between an activated olefin and electrophiles in the presence of a tertiary amine/phosphine. Herein, we present the use of MBH alcohols, which are obtained from the reaction of nitrostyrenes with aldehydes, as well as acetates and amines derived thereof in several organocatalytic transformations. Densely functionalised MBH adducts can also be used to synthesise substituted heteroaromatic compounds, such as furan, pyrrole, pyrazole and imidazole derivatives. SN - 1528-0691 UR - https://www.unboundmedicine.com/medline/citation/27701816/Morita_Baylis_Hillman__MBH__Reaction_Derived_Nitroallylic_Alcohols_Acetates_and_Amines_as_Synthons_in_Organocatalysis_and_Heterocycle_Synthesis_ DB - PRIME DP - Unbound Medicine ER -

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Morita-Baylis-Hillman (MBH) Reaction Derived Nitroallylic Alcohols, Acetates and Amines as Synthons in Organocatalysis and Heterocycle Synthesis.Chem Rec. 2017 Mar; 17(3):363-381.CR