Cationic Iron(III) Salt as an Initiator for Radical Cation‐induced [4+2] Cycloaddition. Issue 3 (30th January 2020)

• Record Type: Journal Article
• Authors: Horibe, Takahiro; Ohmura, Shuhei; Katagiri, Kei; Ishihara, Kazuaki
• Is Part Of: Asian journal of organic chemistry. Volume 9:Issue 3(2020)
• Page Start: 395
• Page End: 398
• Publication Date: 2020-01-30
• Subjects: iron(III) salt -- radical cation -- [4+2] cycloaddition -- α, β-unsaturated carbonyl compound -- anethole; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900749
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: We developed a cationic iron(III) salt initiator for radical cation‐induced [4+2] cycloaddition. Fe(OTf)3 [or Fe(ClO4 )3 ] behaves as a highly active oxidant for both electron‐deficient and electron‐rich dienophiles. The scope of substrates is much broader than with FeCl3 reported previously. With highly active Fe(OTf)3, we demonstrate a formal total synthesis of Heitziamide A. Abstract : Radical cation‐induced [4+2] cycloaddition initiated by Fe(OTf)3 or Fe(ClO4 )3 was developed. Fe(OTf)3 or Fe(ClO4 )3 as a highly active one‐electron oxidant promotes [4+2] cycloaddition for both electron‐deficient and electron‐rich p ‐methoxystyrene derivatives as dienophiles. By taking advantage of the high activity of these iron(III) salts, we demonstrate both a 12 gram‐scale synthesis and a formal total synthesis.