74669-75-3

Upstream product

• 67152-34-5 (R)-3-Methyl-2-phenylbutyltosylat 
• 13491-13-9 (R)-2-isopropyl-2-phenylacetic acid 
• 586341-97-1 (3R,4E)-2-methyl-3-phenylhex-4-enoic acid 
• 586341-98-2 (3R,4E)-2-methyl-3-phenylhex-4-en-1-ol 
• 78019-45-1 (S)-(E)-4-Phenyl-5-methyl-2-hexene 
• 81176-43-4 (S)-trans-4-phenyl-3-buten-2-ol 
• 23406-60-2 (2R)-3-methyl-2-phenylbutan-1-ol 

Downstream Products

• 196106-01-1 (R)-3-methyl-2-phenylbutan-1-amine 

Relevant academic research and scientific papers

Enantioselective synthesis of benzylic stereocentres via Claisen rearrangement of enantiomerically pure allylic alcohols: Preparation of (R)- and (S)-3-methyl-2-phenylbutylamine

The Johnson-Claisen rearrangement of enantiopure allylic alcohols in triethylorthopropionate is the key step for the preparation of chiral molecules with benzylic stereogenic carbon atoms bearing an isopropyl moiety. The synthetic procedure is applied to the preparation of (R)- and (S)-3-methyl-2-phenylbutylamine.

Stereochemistry of Aliphatic Carbocations, 15. Rearrangements in 2-Arylalkyl Systems

Phenyl shifts from secondary to primary carbon proceed with virtually complete inversion at the migration origin, regardless whether they are induced by solvolysis of the aryl sulfonate 25 or by deamination of the amines 12, 17, 26, and 43.Sequential rearrangements (Ph, CH3 and Ph, H) are likewise stereo- and regiospecific.These results strongly support the intervention of phenonium ions.In contrast, the competitive alkyl shifts (deamination only) from benzylic to primary carbon produce but a small excess of inversion (Me 27percent, Et 13percent, iPr 20percent, tBu 3percent).Obviously, benzyl cations are the predominant intermediates.