253676-07-2

Upstream product

• 220324-07-2 Methyl (4S,2Z)-2-bromo-4-[N-(4-methoxy-2,3,6-trimethylphenylsulfonyl)amino]-5-phenylpent-2-enoate 
• 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 

Relevant academic research and scientific papers

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.

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.