Catalytic Asymmetric Synthesis of Cyclic Sulfamides from Conjugated Dienes

• Published in: Organic letters Vol. 15; no. 4; pp. 796 - 799
• Main Authors: Cornwall, Richard G, Zhao, Baoguo, Shi, Yian
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 15.02.2013; Amer Chemical Soc
• Subjects: Alkadienes - chemistry; Catalysis; chemical reactions; chemical structure; Chemistry; Chemistry, Organic; Combinatorial Chemistry Techniques; ligands; Molecular Structure; organic compounds; Palladium - chemistry; Physical Sciences; Science & Technology; Sulfonamides - chemical synthesis; Sulfonamides - chemistry; ALKENES; PROMOTED INTRAMOLECULAR DIAMINATION; ELECTROPHILIC DIAMINATION; MECHANISTIC PATHWAYS; CU(I)-CATALYZED REGIOSELECTIVE DIAMINATION; OXIDATIVE DIAMINATION; DIALKYLZINC REAGENTS; INHIBITORS; INTERMOLECULAR DIAMINATION; VICINAL DIAMINATION

This paper describes the catalytic asymmetric diamination of alkyl dienes using N,N′-di-tert-butylthiadiaziridine 1,1-dioxide in the presence of Pd(0) and a chiral phosphoramidite ligand to give cyclic sulfamides in high yield and high ee. The diamination is also amenable to gram scale.