Synthesis of Unnatural Selenocystines and β-Aminodiselenides via Regioselective Ring-Opening of Sulfamidates Using a Sequential, One-Pot, Multistep Strategy

• Published in: Journal of organic chemistry 2010-05, Vol.75 (9), p.2910-2921
• Main Authors: Rashid Baig, Nasir Baig, Chandrakala, R. N, Sudhir, V. Sai, Chandrasekaran, Srinivasan
• Format: Article
• Language: English
• Subjects: Amines - chemical synthesis; Chemistry; Cyanates - chemistry; Cystine - analogs & derivatives; Cystine - chemical synthesis; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Molecular Structure; Molybdenum - chemistry; Organic chemistry; Organometallic Compounds - chemistry; Organoselenium Compounds - chemical synthesis; Peptides; Peptides - chemical synthesis; Peptides - chemistry; Preparations and properties; Selenium Compounds - chemistry
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo1001388

A variety of N-alkyl-β-aminodiselenides have been synthesized in high yield from sulfamidates under mild reaction conditions using potassium selenocyanate and benzyltriethylammonium tetrathiomolybdate ([BnNEt3]2MoS4) in a sequential, one-pot, multistep reaction. The tolerance of multifarious protecting groups under the reaction conditions is discussed. The methodology was successfully extended to the synthesis of selenocystine, 3,3′-dialkylselenocystine, and 3,3′-diphenylisoselenocystine and their direct incorporation into peptides.