Ring-opening reaction of Bus- and SES-protected aziridines using lithiated dithianes.
The scope and limitation of the ring-opening reaction of sulfonyl-activated aziridines using lithiated dithianes was investigated. Nucleophilic attack of lithiated dithianes on aziridines containing tert-butylsulfonyl (Bus) and 2-(trimethylsilyl)ethylsulfonyl (SES) demonstrated efficient ring cleavage to yield beta-amino carbonyl equivalents, gamma-lactam and syn- and anti-1,5-aminoalcohols. The first example of a ring-opening reaction of di-substituted aziridine using dithiane is also reported. Finally, the Bus and SES-possessing dithianes obtained were deprotected to demonstrate their synthetic usefulness.
Sakakibara
Ken
K
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, 113-8656, Tokyo, Japan.
Nozaki
Kyoko
K
D000605:Amino Alcohols / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D011807:Quinolizines / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*; D013457:Sulfur Compounds / Q000737:chemistry*
D000605:Amino Alcohols; D001388:Aziridines; D007769:Lactams; D011807:Quinolizines; D013451:Sulfonic Acids; D013457:Sulfur Compounds; C438055:dithiane; C033132:aziridine; D008094:Lithium