198546-61-1

Basic information

• Product Name: (4-Methoxy-phenyl)-((S)-1-methyl-1-phenyl-but-3-enyl)-carbamic acid tert-butyl ester
• CAS NO: 198546-61-1
• Molecular Weight: 367.488
• Mol File: 198546-61-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (4-Methoxy-phenyl)-((S)-1-methyl-1-phenyl-but-3-enyl)-carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4-Methoxy-phenyl)-((S)-1-methyl-1-phenyl-but-3-enyl)-carbamic acid tert-butyl ester(198546-61-1)
• EPA Substance Registry System: (4-Methoxy-phenyl)-((S)-1-methyl-1-phenyl-but-3-enyl)-carbamic acid tert-butyl ester(198546-61-1)

Safety Data

• Hazardous Substances Data: 198546-61-1(Hazardous Substances Data)

Upstream product

• 41029-45-2 allyl triflate 
• 176211-96-4 (4-Methoxy-phenyl)-((S)-1-phenyl-ethyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

A mechanistic and structural investigation of the (-)-sparteine mediated asymmetric benzylic lithiation substitution reactions of N-Boc-N-(p-methoxyphenyl)benzylamine

Mechanistic and structural studies show the high enantioenrichments in the products from lithiation substitutions of N-Boc-N-(p-methoxyphenyl)benzylamine (1) by n-BuLi/(-)-sparteine (6) arise from an enantioselective deprotonation of 1 to provide configurationally stable (R)-2/6. NMR spectroscopy establishes that 13C, 6Li labeled (R)-2/6 and (S)-2/6 are monomeric with lithium complexed to the benzylic position, the carbonyl of the Boc group and (-)-sparteine. Deprotonations of the tertiary protons in (R)- and (S)-N-Boc-N-(p-methoxyphenyl)-α-methylbenzylamine ((R)-8 and (S)-8) with n-BuLi/TMEDA provide (R)-9/TMEDA and (S)-9/TMEDA, respectively, with high enantioenrichments. Absolute configurations assigned to (R)-2 and (R)-1-d1 allow analysis of the electrophile dependent stereochemistry of the reactions of these configurationally stable organolithium intermediates.