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A new synthetic route for axially chiral secondary amines with binaphthyl backbone and their applications in asymmetric Michael reaction of aldehydes to nitroalkenes.
Org Biomol Chem. 2012 Apr 21; 10(15):3071-9.OB

Abstract

A new synthetic route for binaphthyl-based secondary amines has been developed. The key features of this route include the selective direct esterification of the binaphthyl structure at the 3- or 3,3'-position and the methylation by a Negishi cross-coupling reaction. Based on the new approach, a series of 3-monosubstituted and 3,3'-disubstituted chiral secondary amines with a binaphthyl backbone were synthesized and screened in the Michael reaction of aldehydes to various nitroalkenes. 3-Monosubstituted secondary amine 7c was proved to be the best catalyst, affording high yields (up to 95%), good to excellent enantioselectivities (up to 99%) and diastereoselectivities (syn/anti up to 99:1) under the optimized conditions.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Liang DC
Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, People's Republic of China.
Luo RS
No affiliation info available
Yin LH
No affiliation info available
Chan AS
No affiliation info available
Lu G
No affiliation info available

MeSH

AldehydesAlkenesAminesCatalysisEsterificationMethylationMolecular StructureNaphthalenesNitro CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22395306

Citation

Liang, Da-Cheng, et al. "A New Synthetic Route for Axially Chiral Secondary Amines With Binaphthyl Backbone and Their Applications in Asymmetric Michael Reaction of Aldehydes to Nitroalkenes." Organic & Biomolecular Chemistry, vol. 10, no. 15, 2012, pp. 3071-9.
Liang DC, Luo RS, Yin LH, et al. A new synthetic route for axially chiral secondary amines with binaphthyl backbone and their applications in asymmetric Michael reaction of aldehydes to nitroalkenes. Org Biomol Chem. 2012;10(15):3071-9.
Liang, D. C., Luo, R. S., Yin, L. H., Chan, A. S., & Lu, G. (2012). A new synthetic route for axially chiral secondary amines with binaphthyl backbone and their applications in asymmetric Michael reaction of aldehydes to nitroalkenes. Organic & Biomolecular Chemistry, 10(15), 3071-9. https://doi.org/10.1039/c2ob07110j
Liang DC, et al. A New Synthetic Route for Axially Chiral Secondary Amines With Binaphthyl Backbone and Their Applications in Asymmetric Michael Reaction of Aldehydes to Nitroalkenes. Org Biomol Chem. 2012 Apr 21;10(15):3071-9. PubMed PMID: 22395306.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A new synthetic route for axially chiral secondary amines with binaphthyl backbone and their applications in asymmetric Michael reaction of aldehydes to nitroalkenes. AU - Liang,Da-Cheng, AU - Luo,Ren-Shi, AU - Yin,Li-Hua, AU - Chan,Albert S C, AU - Lu,Gui, Y1 - 2012/03/06/ PY - 2012/3/8/entrez PY - 2012/3/8/pubmed PY - 2012/7/18/medline SP - 3071 EP - 9 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 10 IS - 15 N2 - A new synthetic route for binaphthyl-based secondary amines has been developed. The key features of this route include the selective direct esterification of the binaphthyl structure at the 3- or 3,3'-position and the methylation by a Negishi cross-coupling reaction. Based on the new approach, a series of 3-monosubstituted and 3,3'-disubstituted chiral secondary amines with a binaphthyl backbone were synthesized and screened in the Michael reaction of aldehydes to various nitroalkenes. 3-Monosubstituted secondary amine 7c was proved to be the best catalyst, affording high yields (up to 95%), good to excellent enantioselectivities (up to 99%) and diastereoselectivities (syn/anti up to 99:1) under the optimized conditions. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/22395306/A_new_synthetic_route_for_axially_chiral_secondary_amines_with_binaphthyl_backbone_and_their_applications_in_asymmetric_Michael_reaction_of_aldehydes_to_nitroalkenes_ L2 - https://doi.org/10.1039/c2ob07110j DB - PRIME DP - Unbound Medicine ER -