I plan to try cyclization in a planetary ball mill with Mg, Zn, Li, Na
Sodium in a ball mill, I would love to see that. Might add some permanganate ;)
Have fun
Friedel-Crafts Acylation with N-(Trifluoroacetyl)-?-amino Acid Chlorides. Application to the Preparation of ?-Arylalkylamines and 3-Substituted 1,2,3,4-Tetrahydroisoquinolines
J. E. Nordlander, M. J. Payne, F. G. Njoroge, M. A. Balk, G. D. Laikos, and V. M. Vishwanath
J. Org. Chem., 49(22), 4107-4111.
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(Ref. #13 from https://www.thevespiary.org/rhodium/Rhodium/pdf/nichols/nichols-dragonfly-2.pdf (https://www.thevespiary.org/rhodium/Rhodium/pdf/nichols/nichols-dragonfly-2.pdf)
.)
Abstract
Several N-(trifluoroacetyl)-?-amino acid chlorides have been reacted with PhH, MeOPh, and 1,2-(MeO)2PhH in the presence of AlCl3 or SnCl4 to produce ArCOCH(NHCOCF3)R in fair to high yields. The (trifluoroacetyl)amino group of the products can be N-methylated with MeI/K2CO3 in boiling Me2CO. Reduction of the ketones with H2 - Pd/C in EtOH under neutral conditions resulted in alcohols. Hydrogenation in the presence of HCl led to complete deoxygenation. Reductions with Et3SiH in refluxing CF3COOH or in BF3·Et2O at rt gave alcohols (Ar = Ph) or deoxygenated products (Ar = 4-MeOPh or 3,4-(MeO)2Ph). The products of reduction can be readily detrifluoroacetylated by mild basic hydrolysis and thence converted to the corresponding 3-substituted 1,2,3,4-tetrahydroisoquinolines by condensation with CH2O.
N-(Trifluoroacetyl)-?-amino Acid Chlorides as Chiral Reagents for Friedel-Crafts Synthesis
J. E. Nordlander, F. G. Njoroge, M. J. Payne, and D. Warman
J. Org. Chem., 50, 3481-3484 (1985).
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Abstract
Chiral N-(trifluoroacetyl)-?-amino acid chlorides undergo Friedel-Crafts reaction with PhH and 1,2-(MeO)2PhH under mild conditions commonly with complete (>99%) preservation of configurational identity. The resultant (trifluoroacetyl)amino ketones may be deoxygenated with Et3SiH or H2/Pd-C in acidic media to the corresponding N-(trifluoroacetyl)-?-arylalkylamines likewise without loss of configurational purity.
A Short Enantiospecific synthesis of 2-Amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene (ADTN)
J. E. Nordlander, M. J. Payne, F. G. Njoroge, V. M. Vishwanath, Gi Rin Han, G. D. Laikos, and M. A. Balk
J. Org. Chem., 50, 3619-3622 (1985).
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(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000185131-ADTN_.gif)
A Short Synthesis of (S)-(+)-Tylophorine
J. E. Nordlander† and F. G. Njoroge
J. Org. Chem., 52, 1627-1630 (1987).
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Abstract
Friedel-Crafts acylation of 2,3,6,7-tetramethoxyphenanthrene with (S)-N-(trifluoroacetyl)prolyl chloride (1.2 eq.) followed by deoxygenation of the resultant ketone with Et3SiH in BF3·Et2O at rt, removal of the trifluoroacetyl group (NH3 - MeOH), and Pictet-Spengler cyclomethylenation with CH2O in ethanolic HCl resulted in (S)-(+)-Tylophorine.
Facile Approach to Enantiomerically Pure ?-Amino Ketones by Friedel-Crafts Aminoacylation and Their Conversion into Peptidyl Ketones
Maria Luisa Di Gioia, Antonella Leggio, Angelo Liguori, Anna Napoli, Carlo Siciliano, and Giovanni Sindona
J. Org. Chem., 66(21), 7002-7007 (2001).
DOI:10.1021/jo010414q (http://dx.doi.org/10.1021/jo010414q)
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See also Post 475692 (https://www.thevespiary.org/talk/index.php?topic=11323.msg47569200#msg47569200)
(Rhodium: "A two-step method for chiral cathinones", Novel Discourse).