138212-44-9

Basic information

• Product Name: trans-N-p-toluenesulfonyl-5-t-butyl-4-vinyl-2-oxazolidinone
• Synonyms: trans-N-p-toluenesulfonyl-5-t-butyl-4-vinyl-2-oxazolidinone
• CAS NO: 138212-44-9
• Molecular Weight: 323.413
• Mol File: 138212-44-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: trans-N-p-toluenesulfonyl-5-t-butyl-4-vinyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: trans-N-p-toluenesulfonyl-5-t-butyl-4-vinyl-2-oxazolidinone(138212-44-9)
• EPA Substance Registry System: trans-N-p-toluenesulfonyl-5-t-butyl-4-vinyl-2-oxazolidinone(138212-44-9)

Safety Data

• Hazardous Substances Data: 138212-44-9(Hazardous Substances Data)

Upstream product

• 131141-50-9 O-(1-tert-butyl-2,3-butadienyl) N-tosylcarbamate 
• 122053-44-5 (Z)-2,2-dimethylhex-4-en-3-ol 
• 4083-64-1 Tosyl isocyanate 
• 169260-05-3 1-t-butyl-4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ol 
• 52547-77-0 2,2-dimethyl-4,5-hexadien-3-ol 
• 19550-89-1 2,2-dimethyl-5-hexen-3-ol 
• 188580-98-5 2,2-dimethylhex-5-en-3-yl tosylcarbamate 

Relevant articles and documents

Palladium(II)-catalyzed oxidative cyclization of allylic tosylcarbamates: Scope, derivatization, and mechanistic aspects

A highly selective oxidative palladium(II)-catalyzed (Wacker-type) cyclization of readily available allylic tosylcarbamates is reported. This operationally simple catalytic reaction furnishes tosyl-protected vinyl-oxazolidinones, common precursors to syn-1,2-amino alcohols, in high yield and excellent diasteroselectivity (>20:1). It is demonstrated that both stoichiometric amounts of benzoquinone (BQ) as well as aerobic reoxidation (molecular oxygen) is suitable for this transformation. The title reaction is shown to proceed through overall trans-amidopalladation of the olefin followed by β-hydride elimination. This process is scalable and the products are suitable for a range of subsequent transformations such as: kinetic resolution (KR) and oxidative Heck-, Wacker-, and metathesis reactions.

Silver(I)-catalyzed aminocyclization of 2,3-butadienyl and 3,4-pentadienyl carbamates: An efficient and stereoselective synthesis of 4-vinyl-2-oxazolidinones and 4-vinyltetrahydro-2H-1,3-oxazin-2-ones

Silver(I) salts in combination with an appropriate base (mostly triethylamine) catalyzed the aminocyclization of N-substituted 2,3-butadienyl carbamates 1 (benzene, 50°C) to provide 4-vinyl-2-oxazolidinones 2 in good yields. The stereoselectivity (trans-2/cis-2) ranged from 1.4 for C5-Me to >30 for C5-phenyl, isopropenyl, and t-butyl derivatives. 3,4-Pentadienyl tosylcarbamates 3, the one-carbon higher homologues of 1, underwent a similar cyclization to give 4-vinyltetrahydro-2H-1,3-oxazin-2-one 4 in synthetically useful yields and in higher trans selectivities than 1.