A convenient preparation of diastereomerically pure, diversely substituted piperazine-2,5-diones from n-protected -amino acids

Synthesis

Volumn , Issue 15, 2010, Pages 2527-2532

  Nikulnikov, Mikhail ^a,b   Shumsky, Alexei ^a   Krasavin, Mikhail ^a,b  

^a YAROSLAVL STATE PEDAGOGICAL UNIVERSITY   (Russian Federation)

^b Chemical Diversity Research Institute   (Russian Federation)

Author keywords

enolization; microwave assisted; piperazine 2,5 diones; post Ugi modification; Ugi multicomponent reaction

Indexed keywords

DEPROTECTION; DIASTEREOMERS; ENOLIZATION; EQUILIBRATION PROCESS; HIGH TEMPERATURE; MICROWAVE-ASSISTED; MOLECULAR MECHANICS CALCULATIONS; PRODUCT MIXTURE; TERT-BUTYL ISOCYANIDE; UGI MULTICOMPONENT REACTION; UGI REACTION;

ACETIC ACID; ALDEHYDES; AMINATION; AMINO ACIDS; CYANIDES; ORGANIC ACIDS; PH EFFECTS; STEREOCHEMISTRY;

CYCLIZATION;

ACETIC ACID; ALDEHYDE; ALPHA AMINO ACID; AMINE; CYANAMIDE; PIPERAZINE DERIVATIVE;

ARTICLE; CYCLIZATION; DEPROTECTION REACTION; DIASTEREOISOMER; MOLECULAR MECHANICS; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 77954950390     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218829     Document Type: Article

References (14)

1. (a) For a comprehensive review, see:, Akritopoulou-Zanze I, Djuric S W., Heterocycles 2007 73 125
2. (b) Wu J, Yong J, Dai W.-M, Synlett 2009 1162
3. (c) Hulme C, Chapetta S, Griffith C, Lee Y.-S, Dietrich J, Tetrahedron Lett. 2009 50 1939
4. (d) Erb W, Neuville L, Zhu J, J. Org. Chem. 2009 74 3109
5. (e) Basso A, Banfi L, Guanti G, Riva R, Org. Biomol. Chem. 2009 7 253
6. Nikulnikov M, Tsirulnikov S, Kysil V, Ivachtchenko A, Krasavin M, Synlett 2009 260
7. (a) For selected reports on convertible isocyanides, see:, Keating T A., Armstrong R W., J. Am. Chem. Soc. 1995 117 7842
8. (b) Rikimaru K, Yanagisawa A, Kan T, Fukuyama T, Synlett 2004 41
9. (c) Isaacson J, Gilley C B., Kobayashi Y, J. Org. Chem. 2007 72 3913
10. (d) Blackburn C, Guan B, Tetrahedron Lett. 2000 41 1495
11. Hulme C, Chapetta S, Dietrich J, Tetrahedron Lett. 2009 50 4054
12. The 1H NMR spectra (300 MHz, DMSO-d6) of the crude products 2 displayed strongly broadened signals when run at ambient temperature, most likely, due to restricted amide bond rotation. On running some of the spectra at increased temperature (314 K), it was possible to confirm that products 2 were obtained as equal mixtures of diastereomers, as would be expected from the non-diastereoselective course of the Ugi reaction.
13. Sigma-Aldrich chemistry products catalogue: www.sigmaaldrich.com
14. Molecular mechanics (MM2) calculations were performed using ChemBio3D Ultra 11.0, CambridgeSoft.