The Hive > Serious Chemistry

The reason to use a PTC is to have the anion...

<< < (2/2)

azole:
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.

(Ref. #13 from 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).


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).




A Short Synthesis of (S)-(+)-Tylophorine
J. E. Nordlander† and F. G. Njoroge
J. Org. Chem., 52, 1627-1630 (1987).


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




   See also Post 475692 (Rhodium: "A two-step method for chiral cathinones", Novel Discourse).

Organikum:
The link in scarmanis post Post 514666 (missing) (scarmani: "Et3SiH / TFA Reduction - Improvements?", Serious Chemistry) to the uploaded article is broken. Not the DOI which leads to a download for registered users only but the link to the uploaded file here on the board.

regards
ORG

java:
OrganikumI think you meant to post on the serious chemistry Phenylalanine to
amphetamine.... I have the article , do you want me to upload it ....java

Edit: I uploaded it on the Phenylalanine to a
amphetamine thread......java

Navigation

[0] Message Index

[*] Previous page