Switching Diastereoselectivity in Catalytic Enantioselective (3+2) Cycloadditions of Azomethine Ylides Promoted by Metal Salts and Privileged Segphos-Derived Ligands
نویسندگان
چکیده
منابع مشابه
Catalytic Enantioselective 1,3-Dipolar Cycloadditions of Azomethine Ylides for Biology-Oriented Synthesis
Cycloaddition reactions are among the most powerful methods for the synthesis of complex compounds. In particular, the development and application of the 1,3-dipolar cycloaddition, an important member of this reaction class, has grown immensely due to its powerful ability to efficiently build various five-membered heterocycles. Azomethine ylides are commonly used as dipoles for the synthesis of...
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Catalytic, enantioselective [3 + 2] cycloadditions of azomethine ylides derived from alanine imino esters with 3-nitroindoles are reported. The dearomative cycloaddition reactions occur in the presence of a catalyst generated in situ from Cu(OTf)2 and (R)-Difluorphos to form exo’-pyrroloindoline cycloadducts and establish four contiguous stereogenic centers, two of which are fully substituted. ...
متن کاملCopper(II)-catalyzed exo and enantioselective cycloadditions of azomethine imines.
A strategy for exo and enantioselective 1,3-dipolar cycloaddition of azomethine imines to 2-acryloyl-3-pyrazolidinone is described. The corresponding cycloadducts are isolated with high diastereoselectivities (up to >96:4 exo/endo) and enantioselectivities (up to 98% ee).
متن کاملOrganocatalytic enantioselective (3+2) cycloaddition using stable azomethine ylides.
We have developed a highly efficient procedure for carrying out the catalytic enantioselective (3+2) cycloaddition between enals and stable azomethine ylides such as isoquinolinium and phthalizinium methylides. Under the optimized reaction conditions highly substituted chiral pyrroloisoquinolines and pyrrolophthalazines have been obtained in high yields and excellent diastereo- and enantioselec...
متن کاملCatalytic chemoselective [3+3] cycloadditions of azomethine ylides with quinone monoimides leading to the construction of a dihydrobenzoxazine scaffold.
A chemoselective [3+3] cycloaddition of in situ generated azomethine ylides with quinone monoimides has been established, which efficiently led to the construction of dihydrobenzoxazine frameworks with biological relevance, with excellent chemoselectivities and high yields (up to >95 : 5 cr and 98% yield).
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2019
ISSN: 0022-3263,1520-6904
DOI: 10.1021/acs.joc.9b00267