289710-09-4

Basic information

• Product Name: (1R,2S,3S)-3-[N-(tert-butoxycarbonyl)-amino]-2-ethynyl-4-methyl-1-phenyl-pentan-1-ol
• Synonyms: (1R,2S,3S)-3-[N-(tert-butoxycarbonyl)-amino]-2-ethynyl-4-methyl-1-phenyl-pentan-1-ol
• CAS NO: 289710-09-4
• Molecular Weight: 317.428
• Mol File: 289710-09-4.mol

Chemical Properties

• CAS DataBase Reference: (1R,2S,3S)-3-[N-(tert-butoxycarbonyl)-amino]-2-ethynyl-4-methyl-1-phenyl-pentan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,3S)-3-[N-(tert-butoxycarbonyl)-amino]-2-ethynyl-4-methyl-1-phenyl-pentan-1-ol(289710-09-4)
• EPA Substance Registry System: (1R,2S,3S)-3-[N-(tert-butoxycarbonyl)-amino]-2-ethynyl-4-methyl-1-phenyl-pentan-1-ol(289710-09-4)

Safety Data

• Hazardous Substances Data: 289710-09-4(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 253676-32-3 (2S,3S)-N-(tert-Butoxycarbonyl)-2-ethynyl-3-isopropylaziridine 
• 253676-31-2 (2R,3S)-N-(tert-Butoxycarbonyl)-2-ethynyl-3-isopropylaziridine 

Relevant articles and documents

Umpolung of chiral 2-ethynylaziridines: Indium(I)-mediated stereoselective synthesis of nonracemic 1,3-amino alcohols bearing three chiral centers, catalyzed by palladium(0)

matrix presented R1 = alkyl, R2 = SO2Ar or Boc, R = alkyl or Ph Treatment of 3-alkyl-2-ethynylaziridines with InI in the presence of Pd(PPh3)4 and H2O gave allenylindium reagents bearing a

2-Ethynylaziridines as chiral carbon nucleophiles: Stereoselective synthesis of 1,3-amino alcohols with three stereocenters via allenylindium reagents bearing a protected amino group

Allenylindium reagents bearing a protected amino group were effectively prepared from N-protected 3-alkyl-2-ethynylaziridines by treatment with InI in the presence of Pd(PPh3)4 and H2O. Stereo-selective addition of the allenylindium to aliphatic or aromatic aldehydes affords 1,3-amino alcohols bearing three contiguous chiral centers: while 2,3-trans-2-ethynylaziridines yield syn,syn-2-ethynyl-1,3-amino alcohols predominantly, 2,3-cis-aziridines give anti,syn isomers selectively. Synthesis of highly substituted ethynylazetidines is also described.