220324-07-2

Upstream product

• 253675-99-9 Methyl (4S,2Z)-2-bromo-4-[N-(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 72155-45-4 Boc-L-phenylalaninal 
• 3182-95-4 L-Phenylalaninol 
• 80745-07-9 4-methoxy-2,3,6-trimethylbenzenesulfonyl chloride 

Downstream Products

• 220324-11-8 (4S,2Z)-2-Bromo-4-[N-(4-methoxy-2,3,6-trimethylphenylsulfonyl)amino]-5-phenylpent-2-en-1-ol 
• 220324-16-3 (4S,2Z)-2-Bromo-O-methylsulfonyl-4-[N-(4-methoxy-2,3,6-trimethylphenylsulfonyl)amino]-5-phenylpent-2-en-1-ol 
• 253676-08-3 (2R,3S)-3-Benzyl-2-ethynyl-N-(4-methoxy-2,3,6-trimethylphenylsulfonyl)aziridine 
• 253676-07-2 (2S,3S)-3-Benzyl-2-ethynyl-N-(4-methoxy-2,3,6-trimethylphenylsulfonyl)aziridine 

Relevant academic research and scientific papers

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.