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Organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane.
Org Lett. 2007 Mar 01; 9(5):943-5.OL

Abstract

[reaction: see text] The first organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane has been realized by using cupreine (2) or 9-O-benzylcupreine (3) as the catalyst. Both catalysts are highly reactive and highly enantioselective. alpha-Hydroxy-beta-nitrophosphonates have been synthesized in good yields and excellent enantioselectivities (>or=90% ee) at a low catalyst loading (5 mol %). These nitroaldol products may be reduced to the biologically significant beta-amino-alpha-hydroxyphosphonates with complete retention of the stereochemistry.

Authors+Show Affiliations

Mandal T
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA.
Samanta S
No affiliation info available
Zhao CG
No affiliation info available

MeSH

CatalysisMethaneMolecular StructureNitrogenNitroparaffinsPhosphorusStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17284048

Citation

Mandal, Tanmay, et al. "Organocatalytic Highly Enantioselective Nitroaldol Reaction of Alpha-ketophosphonates and Nitromethane." Organic Letters, vol. 9, no. 5, 2007, pp. 943-5.
Mandal T, Samanta S, Zhao CG. Organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane. Org Lett. 2007;9(5):943-5.
Mandal, T., Samanta, S., & Zhao, C. G. (2007). Organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane. Organic Letters, 9(5), 943-5.
Mandal T, Samanta S, Zhao CG. Organocatalytic Highly Enantioselective Nitroaldol Reaction of Alpha-ketophosphonates and Nitromethane. Org Lett. 2007 Mar 1;9(5):943-5. PubMed PMID: 17284048.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane. AU - Mandal,Tanmay, AU - Samanta,Sampak, AU - Zhao,Cong-Gui, Y1 - 2007/02/07/ PY - 2007/2/8/pubmed PY - 2007/5/1/medline PY - 2007/2/8/entrez SP - 943 EP - 5 JF - Organic letters JO - Org Lett VL - 9 IS - 5 N2 - [reaction: see text] The first organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane has been realized by using cupreine (2) or 9-O-benzylcupreine (3) as the catalyst. Both catalysts are highly reactive and highly enantioselective. alpha-Hydroxy-beta-nitrophosphonates have been synthesized in good yields and excellent enantioselectivities (>or=90% ee) at a low catalyst loading (5 mol %). These nitroaldol products may be reduced to the biologically significant beta-amino-alpha-hydroxyphosphonates with complete retention of the stereochemistry. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17284048/Organocatalytic_highly_enantioselective_nitroaldol_reaction_of_alpha_ketophosphonates_and_nitromethane_ L2 - https://doi.org/10.1021/ol070209i DB - PRIME DP - Unbound Medicine ER -