Enantioselective Phospha-Michael Reaction of Diphenyl Phosphonate with Nitroolefins Utilizing Conformationally Flexible Guanidinium/Bisthiourea Organocatalyst: Assembly-State Tunability in Asymmetric Organocatalysis

A catalytic enantioselective phospha‐Michael reaction of diphenyl phosphonate to nitroolefins was achieved by utilizing a 1,3‐diamine‐tethered guanidinium/bisthiourea organocatalyst. The procedure is applicable to nitroolefins having various aromatic and aliphatic substituents, and enables an effici...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2011-10, Vol.353 (14-15), p.2631-2636
Main Authors: Sohtome, Yoshihiro, Horitsugi, Natsuko, Takagi, Rika, Nagasawa, Kazuo
Format: Article
Language:English
Subjects:
Aliphatic compounds
asymmetric synthesis
Asymmetry
Catalysis
Catalysts
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
guanidinium species
Organic chemistry
organocatalysis
Organometalloidal and organometallic compounds
P derivatives
phospha-Michael reaction
Phosphonates
Preparations and properties
Synthesis
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
thioureas
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Summary:A catalytic enantioselective phospha‐Michael reaction of diphenyl phosphonate to nitroolefins was achieved by utilizing a 1,3‐diamine‐tethered guanidinium/bisthiourea organocatalyst. The procedure is applicable to nitroolefins having various aromatic and aliphatic substituents, and enables an efficient access to phospha‐Michael products with 90–98% ee. Monomeric or oligomeric active species of the catalyst can be utilized, depending on the presence or absence of water.
ISSN:1615-4150
1615-4169
1615-4169
DOI:10.1002/adsc.201100219