774596-70-2

Upstream product

• 90-85-7 (1R,2S)-1-phenyl-2-(N-methyl-N-benzylamino)propan-1-ol 
• 774596-75-7 (3R,4R)-3-hydroxymethyl-2-methyl-4-(4-methylthiophenyl)-1,2,3,4-tetrahydroisoquinoline 
• 774596-76-8 (3R,4R)-3-chloromethyl-2-methyl-4-(4-methylthiophenyl)-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Enantiospecific Stereodivergent Synthesis of trans- and cis-N(2), 3-Dimethyl- 4-phenyl-1, 2, 3, 4-tetrahydroisoquinolines

The acid-promoted cyclizations of a range of N-benzylethanolamines (derived from pseudoephedrine or ephedrine) give the corresponding trans-N(2), 3-dimethyl-4-phenyl-1, 2, 3, 4- tetrahydroisoquinolines with high levels of diastereoselectivity and in good yields of isolated product. The cyclizations of the corresponding chromium tricarbonyl complexes are rendered completely stereoselective. Acidpromoted cyclization of N-(3′, 4′- dimethoxybenzyl) ephedrine and its chromium tricarbonyl complex occur with complementary diastereoselectivities to give trans- and cis-N(2), 3-dimethyl-4- phenyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydro- isoquinoline, respectively, in >99:1 d.r. The latter is consistent with a "double inversion" mechanism, which involves neighboring group participation by the chromium tricarbonyl moiety followed by rearomatization to give the corresponding cis-tetrahydroisoquinoline with overall retention of configuration.

Transformation of (+)-thiomicamine into chiral non-racemic 3,4-dihydroisoquinolinium salts: Application for catalytic asymmetric epoxidation of alkenes and oxidation of sulfides

(1S,2S)-(+)-Thiomicamine 7 (R = SCH3) has been transformed into (3S,4R)-2,3-dimethyl-4-phenyl-3,4-dihydroisoquinolinium tetrafluoroborate 2 in a five-step reaction sequence involving (3S,4R)-2,3-dimethyl-1,2,3,4- tetrahydroisoquinoline 14 as the key intermediate. Iminium salt 16 has been evaluated as a promoter of catalytic asymmetric epoxidation of trans-stilbene and oxidation of methyl-p-tolyl sulfide, affording products in satisfactory yield and with enantioselectivities up to 45% and 42% ee, respectively.