Organocatalysts Promote Enantioselective 1,3-Dipolar Cycloadditions of Nitrones with 1-Cycloalkene-1-carboxaldehydes

• In the presence of enantiopure organocatalysts, 1-cycloalkene-1-carboxaldehydes and various nitrones furnished fused isoxazolidines. Thus, some chiral pyrrolidinium salts catalyzed the formation of such cycloadducts in high diastereo- and enantioselectivity (up to 92% ee). The predominant diastereomer, the exo one, was mostly obtained in excellent diastereoselectivity (> 99:1 dr). Furthermore, after recrystallization of one of the cycloadducts, this was obtained enantiomerically pure (> 99% ee). The absolute configuration of one of the cycloadducts was determined. 

Subject headings

NATURVETENSKAP  -- Kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

Keyword

dipolar cycloadditions

Chemistry

Kemi

Publication and Content Type

ref (subject category)

art (subject category)