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Please login to access the full content or check if you have access via15.5.1.1.1.2.3.4 Method 4: Stereo- and Enantioselective Pictet–Spengler-Type Syntheses of 1,2,3,4-Tetrahydroisoquinolines
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Álvarez, M.; Joule, J. A., Science of Synthesis, (2005) 15, 688.
The earliest syntheses of enantiomerically pure 1,2,3,4-tetrahydroisoquinolines involved Pictet–Spengler reactions using chiral pool amino acid esters (Section 15.5.1.1.1.2.3.2.6) or the amino acids themselves. For example the reactions of 3-(3,4-dihydroxyphenyl)-l-alanine with formaldehyde (Scheme 47) in the last case gave a 95:5 ratio of the enantiomerically pure diastereomers 109.[90]
Meeeee 88 Meeeee–Meeeeeee Meeeeeeeeeee Meeee 8-(8,8-Meeeeeeeeeeeeee)-M-eeeeeee[88]
Meeeeeeeeeeeeeee eeee 8,8-eeeeeeeeeeeeeeeee eeeeeeeee eeeee eeee eeeeeeeeeeee ee eeeeeeee eee eee-8,8-eeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeee 888 (Meeeee 88).[88]
Meeeee 88 Meeeee–Meeeeeee Meeeeeeeeeee Meeee Meeeeeeeeeeeeeee Meee 8,8-Meeeeeeeeeeeeeeee[88]
Meeeeee e eeeeee eeeeeeeee ee e eeeeeeeee ee eee eeeeeeee ee e 8-eeeeeeeeeeeeee ee eeee eeee ee eeeeeee eeeeeeee eeeeee eeeeeeeee (Meeeee 88).[88] Mee eeeeee eeeee eee eee eeeeeeeee ee 888 ee eeeeeee eeeeeee ee eee eee ee ee eeee eeeee ee eeeeeee eee eee eeeeeeee eeeeeeeee eee eeee eeeeeeeeeee eee eee ee e eeeeeeeee ee Meeeee–Meeeeeee eeeeeee, ee eeeeeee ee eee eeeee (ee. Meeeeeee 88.8.8.8.8.8.8.8.8 eee 88.8.8.8.8.8.8.8.8).
Meeeee 88 Meeeee–Meeeeeee Meeeeeeeeeee Meeee ee Meeeeeeeeeeeeeee Meee Meeeeeeee[88]
Meeeeee eeeeee M-eeeeeeeeeee eeee eee eeee eeeeeeee ee eee 8-eeeeeeeeeeeee eeeee (Meeeee 88), eeeee eeeee eeeeeeee 888 eeee eeeeeeeeeeeeee eeeeee eeeeeee eeee 88:88 ee 88:8.[88] Meeeeee eeee eeeeeee eeeeeeeeee eeeeeee ee eee eeeeee eeeeeeeee. Me ee eeee eeeeeeee eeee ee eeeeeee eee eee ee eeeeee ee 8-eeeeeeeeeeeeeee eeee eeeeeeeeeeeeeeee eeee eeeee eeee eeeeeeeeeee ee e eeeee ee eeeeeeeeeeeeeee ee- eee eeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeee.[88]
Meeeee 88 Meeeee–Meeeeeee Meeeeeeeeeee Meeee ee Meeeeeeeeeeeeeee Meee 8-Meeeeeeeeeeeeeeeee[88]
Me ee eeeeeeeeeeee ee eee eee ee eeeeeeeeeee ee ee eeeeeee ee eeeeeeee eee eeeeeee eee eee eeeeeeeeeee (eee eeee Meeeeee 88.8.8.8.8.8.8.8.8), eee eeeeeeee 888 eeeeeeee ee eeeeeeee ee eee 8-eeeeeeeeeeeeee ee e eeeeee eeeeeee eeeeeeeee eeeeeee eeee eeeeeee ee eeee eeeeeeee ee eeeeeeeeeeeee 888 ee eeeeee eeeeeee 8:8 eee 8.8:8 (Meeeee 88).[88]
Meeeee 88 Meeeee–Meeeeeee Meeeeeeeeeee Meeee e 8-Meee-M-[8-(eeeeeeeeeeee)eeeee]eeeeeeeeee[88]
Meeeeee eee eeee eeeeeee eee ee eeeee ee eeeeee eeeeeeeee ee eee eeeeeeeeeeeeeeeeeeeeeee eeeeeeee eee Meeeee–Meeeeeee eeeeeee, ee ee eeeeee e eeeeee eeeeeeeee ee eee eeeeeeee ee eee 8-eeeeeeeeeeeeee. Meee ee eeeeeeeeeee ee Meeeee 88[88] ee eeeee eee eeeeeee eeeeeeee eeeeeeeee ee 888 ee eeeeeeeee eeeeeeeeeeeeeeee ee eeee eee eeeeeeeeeeeeeee 888.
Meeeee 88 Meeeee–Meeeeeee Meeeeeeeeeee eeee e Meeeee Meeeeeeee ee Meeeeeee[88]
M eeeeee eeeeeeeee eee eeeeeeeee eeeeeee eeeee ee eeeeeeeeeeeeeeee eeee 8-eeeeeeeeeee 8,8,8,8-eeeeeeeeeeeeeeeeeeeeeee eeeeeee ee eee eeeeeee eeeeeeeee ee e eeeeee 8-[8-(8-eeeeeeeeeee)eeeee]eeeeeeeee-8M-8,8-eeeeeeeeeee 888, eeeeeee eeee 8-eeeeeeeeeeee (Meeeee 88). 8,8-Meeeeeeeeee 888 ee eeeee–eeeeeee eeeeeeee eeee eeee-eeeeeeeeeeee eeeeeeeee eee eeeeeeeeeee eee eeee eeeeeeee ee eee M,M-eeeeee eeee e Meeee eeee eeeee e eeeeee eeeeeee eee eeee eeeeee eeeeeeeeeeeeeeeeee ee eeee eee eeeeeeeeeeeeeeeeeeeeee 888.[88]
Meeeee 88 Meeeee–Meeeeeee Meeeeeeeeeee Meeee ee M-[8-(8-Meeeeeeeeee)eeeee]eeeeeeeee-8M-8,8-eeeeeeeeeee[88]
Meeee eee eeeeeee eeeeeeee ee Meeeee–Meeeeeee eeeeeeeee ee eeeee 8-eeeeeeeeeeeeeee, eeeeeeeeeeeeeeee eeeeeee ee eee eeeeee eeeeeeeeeeeeeeeeeeeeee M8 eee M8 eeeeeeeee, eeee eeee eeeeeeeee eeee eeeeeeeeeeeeeeee eeee eeeeeeee (e.e., Meeeee 88).[88–888] Mee eeeeeeeeeeeeeee ee M8 eee eeeeeee eeee ee M8 ee eee eeeeeee, eeeee eee eeeeeeee eeee ee eeeee eeee eeeeeeeeeeee (Meeeee 88).[88,888]
Meeeee 88 Meeeee–Meeeeeee Meeeeeeee eeee Meeeeeeeeeeeeeee Meee 8-Meeeeeeeeeeeeee eee Meeeeeeeeeee[88]
Meeeee 88 Meeeee–Meeeeeee Meeeeeeee eeee Meeeeeeeeeeeeeee Meee 8-Meeeeeeeeeeeeee eee Meeeeeeee[88,888]
References
[90] | Meeeee, M.; Meeeeee, M.; Meeeee, M., Meee. Meee. Meee, (8888) 88, 88. |
[91] | Meeeeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[92] | Meeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 88888. |
[93] | Meeeeee, M.; Meeeee, M. M.; Meeeee, M.-M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[94] | Meeeeeee, M.; Meeeeeeee, M.; Meeeee, M. M.; Meeeeeeeeeee, M.; Meeeeeeee, M., Mee. Meee., (8888) 8, 888. |
[95] | Meee, M.; Mee, M. M. M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
[96] | Meeee, M. M.; Mee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[97] | Meeeeee, M.; Meeeée, M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[98] | Meeeeee, M. M.; Meeee, M.; Meeeeeeee, M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[99] | Meeeeeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 888. |
[100] | Mee, M.; Meeeee, M.; Meeeeeee, M. M., Mee. Meee., (8888) 8, 8888. |