253676-34-5

Upstream product

• 253676-17-4 (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-ol 
• 253676-15-2 (3S,4S)-4-[N-(tert-Butoxycarbonyl)amino]-5-(tert-butyldimethylsiloxy)-1-trimethylsilylpent-1-yn-3-ol 
• 253676-18-5 (2S,3S)-2-[N-(2,4,6-Trimethylphenylsulfonyl)amino]-5-trimethylsilylpent-4-yne-1,3-diol 
• 140200-05-1 tert-butyl (S)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 126645-26-9 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate 
• 253676-19-6 (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-1-yn-3-ol 

Relevant academic research and scientific papers

A highly cis-selective synthesis of 2-ethynylaziridines by intramolecular amination of chiral bromoallenes: Improvement of stereoselectivity based on the computational investigation

The base-mediated intramolecular amination of bromoallenes having an axial chirality is described. The treatment of (4S,aR)-4-alkyl-4-[N-(arylsulfonyl)amino]-1-bromobuta-1,2-dienes with NaH in DMF affords 2,3-cis-2-ethynylaziridines in good to excellent s

Stereoselective synthesis of chiral 2,3-cis-2-ethynylaziridines by base-mediated intramolecular amination of bromoallenes

(matrix presented) from (S,aS) 2,3-cis:trans = 79:21-89:11 (76-93% yield) from (S,aR) 2,3-cis:trans = 91:9-99:1 (50-99% yield) Novel stereoselective synthesis of 2,3-cis-2-ethynylaziridines from amino allenes is presented. While sodium hydride mediated intramolecular amination of (4S,aS)-4-alkyl-4-[N-(arylsulfonyl)amino]-1-bromobuta-1,2-dienes yields a mixture of 2,3-cis- and 2,3-trans-2-ethynylaziridines in which the cis-isomer predominates (79:21-89:11), the amination of (4S,aR)-isomers affords 2,3-cis-aziridines in excellent selectivities (91:9-100:0). Conversion of 2,3-trans-2-ethynylaziridines into the corresponding cis-isomers via a sequence of reactions (methanesulfonic acid mediated ring-opening reaction, bromination, and aziridination) is also described.

Convenient syntheses of chiral 3-substituted 2-ethynylaziridines

Two convenient methods for the synthesis of chiral 2-ethynylaziridines from natural α-amino acids are described. Sodium hydride-promoted aziridination of mesylates of 4-arylsulfonylamino-2-bromoalk-2-en-1-ols yields trans-2-(1-bromovinyl)aziridines in a highly stereoselective manner, and subsequent dehydrobromination of the aziridines by potassium tert-butoxide gives separable stereoisomeric mixtures of trans- and cis-2-ethynylaziridines in enantiomerically pure forms (>98% ee). Simple synthesis of 2-ethynylaziridines with high optical purities (91-98% ee) from chiral amino alcohols bearing an ethynyl group under Mitsunobu conditions is also presented. The Royal Society of Chemistry 1999.