956101-46-5

Basic information

• Product Name: tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidocarbonate
• Synonyms: tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidocarbonate
• CAS NO: 956101-46-5
• Molecular Weight: 233.31
• Mol File: 956101-46-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidocarbonate(956101-46-5)
• EPA Substance Registry System: tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidocarbonate(956101-46-5)

Safety Data

• Hazardous Substances Data: 956101-46-5(Hazardous Substances Data)

Upstream product

• 4248-19-5 tert-butyl carbazate 
• 124517-47-1 cinnamyl tert-butyl carbonate 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 125414-45-1 (2R,3R)-3-<(tert-butoxycarbonyl)amino>-3-phenyl-1,2-propanediol 
• 956101-42-1 C₆H₅C₃H₄NC₂H₃OC₅H₉O₂ 
• 956101-44-3 C₆H₅C₃H₄NC₈H₇O₂C₅H₉O₂ 
• 913344-44-2 (-)-di-tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidodicarbonate 

Downstream Products

• 33125-05-2 Boc-D-Phg-OH 
• 137284-11-8 (2R)-2-N-(tert-butoxycarbonyl)amino-2-phenylethanal 
• 67341-01-9 (R)-N-(tert-butoxycarbonyl)phenylglycinol 
• 148701-46-6 cis-(3S)-hydroxy-(2S)-phenylpiperidine 
• 1284206-61-6 tert-butyl N-(but-2-yn-1-yl)-N-[(1S)-1-phenylprop-2-en-1-yl]carbamate 
• 190189-97-0 methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropionate 
• 103365-47-5 (S)-3-(tert-butoxycarbonylamino)-3-phenylpropanoic acid 
• 718611-17-7 S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

Iridium-catalyzed asymmetric allylic substitutions with bulky amines/oxidative double bond cleavage - Entry into the reetz synthesis of amino alcohols

Branched allylic amines were prepared by Ir-catalyzed enantioselective allylic aminations with the bulky N-nucleophiles HN(Boc)2 and HNBn2. The products were transformed into N-protected amino aldehydes, which were either reduced or coupled diastereoselectively with organometallic compounds to give vicinal amino alcohols. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application. Ir-catalyzed enantioselective allylic aminations with bulky N-nucleophiles HN(Boc)2 and HNBn2 gave N-protected allylic amines, which were transformed into N-protected chiral amino aldehydes. These are useful chiral building blocks as previously demonstrated by Reetz et al. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application.

Direct, intermodular, enantioselective, iridium-catalyzed allylation of carbamates to form carbamate-protected, branched allylic amines

The direct reaction between carbamates and achiral allylic carbonates to form branched, conveniently protected primary allylic amines with high regioseiectivity and enantioselectivity Is reported. This process occurs without base or with 0.5 equiv K3PO4 In the presence of a metalacyclic iridium catalyst containing a labile ethylene ligand. The reactions of aryl-, heteroaryl-, and alkyl-substituted allylic carbonates with BocNH 2, FmocNH2, CbZNH2, TrocNH2, TeocNH2, and 2-oxazolidinone occur In good yields, with high selectivity for the branched isomer and high enantioselectivities (98% average ee).

A Concise Enantioselective Synthesis of Allylamines and N-Boc-β-Amino Acids

A new and efficient enantioselective synthesis of allylamines and N-Boc-β-amino acids has been developed.Starting from enantiomerically enriched N-diphenylmethyl-3-amino-1,2-diols, allylamines are easily obtained by a Corey-Hopkins deoxygenative protocol.After a change in the nitrogen protecting group, the resulting N-Boc allylamines are converted into β-amino acids by hydroboration with 9-BBN followed by oxidation with PDC in DMF.