220765-48-0

Upstream product

• 220324-04-9 Methyl (4S,2Z)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate 
• 220324-08-3 (4S,2Z)-2-Bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-en-1-ol 
• 253676-13-0 (3R,4S)-5-methyl-4-[N-(2,4,6-trimethyl-phenylsulfonyl)amino]-1-trimethylsilyl-hex-1-yn-3-ol 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 253676-14-1 (3R,4S)-5-Methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-1-yn-3-ol 
• 220324-12-9 (4S,2Z)-2-Bromo-O-methylsulfonyl-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-en-1-ol 

Downstream Products

• 253676-37-8 (2S,3S)-3-Isopropyl-2-[2-(methoxycarbonyl)ethynyl]-N-(2,4,6-trimethylphenylsulfonyl)aziridine 
• 253676-38-9 (2S,3S)-3-Isopropyl-N-(2,4,6-trimethylphenylsulfonyl)-2-(2-trimethylsilylethynyl)aziridine 
• 220765-18-4 (2R,3S)-2-ethynyl-3-isopropyl-N-(2,4,6-trimethyl-phenylsulfonyl)-aziridine 
• 220765-22-0 (4S)-5-methyl-4-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-1,2-hexadiene 

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.

A convenient synthesis of activated enantiomerically pure 2- ethynylaziridines

2,3-cis- and 2,3-trans-N-Arylsulfonyl-2-ethynylaziridines with high enantiomeric purity have been synthesized. N-Protected amino aldehydes synthesized from natural α-amino acids were successively treated with Ph3P=C(Br)CO2Me, DIBAL, MsCl-Et3N, NaH in DMSO, and tert-BuOK in THF to yield 2-ethynylaziridines in good to high yields.