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• 586-96-9 Nitrosobenzene 
• 933-06-2 1-acetoxycyclopentene 
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• 545376-56-5 1-trichloroacetoxycyclopentene 

Relevant academic research and scientific papers

Enantioselective nitroso aldol reaction catalyzed by quinoxp *silver(I) complex and tin methoxide

A catalytic enantioselective O-nitroso aldol reaction of alkenyl trichloroacetates with nitrosoarenes was achieved using the (R,R)-t-Bu- QuinoxP*AgOAc complex as the chiral catalyst and Bu2Sn(OMe) 2 as the achiral cocatalyst in the presence of methanol. Optically active ?-aminooxy ketones with up to 99% ee were regioselectively obtained in high yields from various alkenyl trichloroacetates of cyclic ketones.

Thieme Chemistry Journal awardees - Where are they now? Dibutyltin dimethoxide catalyzed N-nitrosoaldol reaction of alkenyl trichloroacetate

Nitrosoaldol reaction between alkenyl trichloroacetates and nitrosobenzene has been achieved using dibutyltin dimethoxide as a catalyst, which is regenerated in the presence of methanol. The corresponding α-hydroxyamino ketones (N-adducts) have exclusivel

Enantioselective O- and N-Nitroso Aldol Synthesis of Tin Enolates. Isolation of Three BINAP-Silver Complexes and Their Role in Regio- and Enantioselectivity

The selective generation of three different silver-BINAP catalysts has been achieved via the proper combination of metal/ligand ratio and/or choice of silver salt. Indeed, the X-ray crystallographic study has been used to gain insight into the structure of the catalyst. After the evaluation of each species, 1:1 (AgX·(R)-BINAP) complex was found to be the real active species in the O-selective nitroso aldol reaction. On the other hand, a systematic survey of solvent has shown that the optimal 2:1 (AgX·(R)-BINAP) complex is the effective catalyst in the N-selective pathway. Thus, a new method of generation of the silver-BINAP catalyst and the synthetic transformations provide not only new insights into the developing area of catalytic enantioselective nitroso aldol synthesis but also clear guidance for the design of an effective catalyst. Copyright

Catalytic enantioselective synthesis of α-aminooxy and α-hydroxy ketone using nitrosobenzene

The highly enantioselective and O-selective nitroso aldol reaction of tin enolates 2 and nitrosobenzene (1) has been developed with the use of (R)-BINAP-silver complexes as a catalyst. After the various silver salts were surveyed, the AgOTf and the AgClO4 complex were found to be optimal in the O-selective nitroso aldol reaction in both asymmetric induction (up to 97% ee) and regioselection (O/N = >99/1), affording aminooxy ketone 3. The product 3 can be transformed to α-hydroxy ketone 5 without any loss of enantioselectivity. Thus, the method provides an efficient approach to the catalytic enantioselective introduction of oxygen α- to the carbonyl group. Copyright

Simple synthesis of α-hydroxyamino carbonyl compounds: New scope of the nitroso aldol reaction

(graph presented) The reaction of nitroso compounds with enolates, the nitroso aldol reaction , occurs in high yield to generate α-hydroxyamino carbonyl compounds. Yields range from 42% to 98% with N-selectivity >99:1 from commercially available aromatic or aliphatic nitroso compounds and a variety of alkali metal or tin enolates.