Diastereoselective Synthesis of N-Protected 2,3-Dihydropyrroles via Iron-Catalyzed Cycloisomerization of alpha-Allenic Sulfonamides

• Herein, we report the synthesis of 2,3-dihydropyrroles via an iron-catalyzed intramolecular nucleophilic cyclization of alpha-allenic sulfonamides. A highly diastereoselective variant of the reaction was also developed with the use of 1,2-disubstituted allenamides, which afforded 2,3-dihydropyrroles with diastereomeric ratios of >98:2. Insight into the mechanism was gained through a detailed DFT study, which elucidates the reaction mechanism and rationalizes the high chemoselectivity and diastereoselectivity.

Subject headings

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

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

Keyword

iron catalysis

allenic sulfonamides

diastereoselective reaction

2

3-dihydropyrroles

homogeneous catalysis

Publication and Content Type

ref (subject category)

art (subject category)