Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst.
J Am Chem Soc. 2006 Jun 07; 128(22):7170-1.JA

Abstract

Primary amine-thiourea derivative 1 is an active and highly enantioselective catalyst for the conjugate addition of ketones to nitroalkenes. Broad substrate scope is described, with nitroalkenes bearing either aromatic or aliphatic substituents and a wide variety of ketones shown to be useful reacting partners. Ethyl ketones react preferentially, generating anti products with methyl-bearing stereocenters with good-to-excellent diastereoselectivity. An enamine mechanism is indicated, with cooperative activation of the electrophile by the thiourea and of the ketone by the primary amine.

Authors+Show Affiliations

Huang H

Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.

Jacobsen EN

No affiliation info available

MeSH

AlkenesAminesCatalysisKetonesMolecular StructureNitro CompoundsStereoisomerismThiourea

Pub Type(s)

Journal Article

Research Support, N.I.H., Extramural

Language

eng

PubMed ID

16734464

Citation

Huang, Hongbing, and Eric N. Jacobsen. "Highly Enantioselective Direct Conjugate Addition of Ketones to Nitroalkenes Promoted By a Chiral Primary Amine-thiourea Catalyst." Journal of the American Chemical Society, vol. 128, no. 22, 2006, pp. 7170-1.

Huang H, Jacobsen EN. Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst. J Am Chem Soc. 2006;128(22):7170-1.

Huang, H., & Jacobsen, E. N. (2006). Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst. Journal of the American Chemical Society, 128(22), 7170-1.

Huang H, Jacobsen EN. Highly Enantioselective Direct Conjugate Addition of Ketones to Nitroalkenes Promoted By a Chiral Primary Amine-thiourea Catalyst. J Am Chem Soc. 2006 Jun 7;128(22):7170-1. PubMed PMID: 16734464.

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

TY - JOUR T1 - Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst. AU - Huang,Hongbing, AU - Jacobsen,Eric N, PY - 2006/6/1/pubmed PY - 2007/7/25/medline PY - 2006/6/1/entrez SP - 7170 EP - 1 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 128 IS - 22 N2 - Primary amine-thiourea derivative 1 is an active and highly enantioselective catalyst for the conjugate addition of ketones to nitroalkenes. Broad substrate scope is described, with nitroalkenes bearing either aromatic or aliphatic substituents and a wide variety of ketones shown to be useful reacting partners. Ethyl ketones react preferentially, generating anti products with methyl-bearing stereocenters with good-to-excellent diastereoselectivity. An enamine mechanism is indicated, with cooperative activation of the electrophile by the thiourea and of the ketone by the primary amine. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16734464/Highly_enantioselective_direct_conjugate_addition_of_ketones_to_nitroalkenes_promoted_by_a_chiral_primary_amine_thiourea_catalyst_ DB - PRIME DP - Unbound Medicine ER -

Tags

Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst.J Am Chem Soc. 2006 Jun 07; 128(22):7170-1.JA