Cycloadditions of Donor–Acceptor Cyclopropanes and ‐butanes using S=N‐Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines. Issue 49 (29th October 2021)

• Record Type: Journal Article
• Authors: Oliver, Gwyndaf A.; Loch, Maximilian N.; Augustin, André U.; Steinbach, Pit; Sharique, Mohammed; Tambar, Uttam K.; Jones, Peter G.; Bannwarth, Christoph; Werz, Daniel B.
• Is Part Of: Angewandte Chemie international edition. Volume 60:Issue 49(2021)
• Page Start: 25825
• Page End: 25831
• Publication Date: 2021-10-29
• Subjects: cycloadditions -- cyclopropanes -- donor–acceptor systems -- sulfinylamines -- sulfur diimide; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202106596
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: We present (3+2)‐ and (4+2)‐cycloadditions of donor–acceptor (D–A) cyclopropanes and cyclobutanes with N‐sulfinylamines and a sulfur diimide, along with a one‐pot, two‐step strategy for the formal insertion of HNSO2 into D–A cyclopropanes. These are rare examples of cycloadditions with D–A cyclopropanes and cyclobutanes whereby the 2π component consists of two different heteroatoms, thus leading to five‐ and six‐membered rings containing adjacent heteroatoms. Abstract : By employing (3+2)‐ and (4+2)‐cycloadditions of donor–acceptor (D–A) cyclopropanes and cyclobutanes with N ‐sulfinylamines and sulfur diimides, a variety of isothiazolidines and thiazinanes were synthesized. Use of a sulfinylamine bearing a leaving group, followed by oxidation, led to formal insertion of HNSO2 providing γ‐sultams with no N ‐substitution.