701974-81-4Relevant articles and documents
Enantioselective nitroso aldol reaction catalyzed by quinoxp *silver(I) complex and tin methoxide
Yanagisawa, Akira,Takeshita, Satoshi,Izumi, Youhei,Yoshida, Kazuhiro
supporting information; experimental part, p. 5328 - 5329 (2010/06/19)
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.
Enantioselective O- and N-Nitroso Aldol Synthesis of Tin Enolates. Isolation of Three BINAP-Silver Complexes and Their Role in Regio- and Enantioselectivity
Momiyama, Norie,Yamamoto, Hisashi
, p. 5360 - 5361 (2007/10/03)
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
Simple synthesis of α-hydroxyamino carbonyl compounds: New scope of the nitroso aldol reaction
Momiyama, Norie,Yamamoto, Hisashi
, p. 3579 - 3582 (2007/10/03)
(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.
