Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
15.5.1.1.1.2.3.4 Method 4: Stereo- and Enantioselective Pictet–Spengler-Type Syntheses of 1,2,3,4-Tetrahydroisoquinolines

DOI: 10.1055/sos-SD-015-01146

Álvarez, M.; Joule, J. A.Science of Synthesis, (200515688.

The earliest syntheses of enantiomerically pure 1,2,3,4-tetrahydroisoquinolines involved PictetSpengler 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 MeeeeeMeeeeeee 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 MeeeeeMeeeeeee 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 MeeeeeMeeeeeee 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 MeeeeeMeeeeeee 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 MeeeeeMeeeeeee 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 MeeeeeMeeeeeee 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 MeeeeeMeeeeeee 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 MeeeeeMeeeeeee 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 eeeeeeeeeeee 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 MeeeeeMeeeeeee Meeeeeeeeeee Meeee ee M-[8-(8-Meeeeeeeeee)eeeee]eeeeeeeee-8M-8,8-eeeeeeeeeee[‌88‌]

Meeee eee eeeeeee eeeeeeee ee MeeeeeMeeeeeee 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).[‌88‌‌888‌] 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 MeeeeeMeeeeeee Meeeeeeee eeee Meeeeeeeeeeeeeee Meee 8-Meeeeeeeeeeeeee eee Meeeeeeeeeee[‌88‌]

Meeeee 88 MeeeeeMeeeeeee Meeeeeeee eeee Meeeeeeeeeeeeeee Meee 8-Meeeeeeeeeeeeee eee Meeeeeeee[‌88‌,‌888‌]

References


Cookie-Einstellungen