Construction of quaternary stereocenters: Asymmetric α-amination of branched aldehydes catalyzed by monoimide substituted cyclohexane-1,2-Diamines

Chirality

Volumn 25, Issue 10, 2013, Pages 668-672

  Fu, Ji Ya ^a,b   Wang, Qi Lin ^a,c   Peng, Lin ^a,c   Gui, Yong Yuan ^a   Xu, Xiao Ying ^a   Wang, Li Xin ^a  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b HENAN UNIVERSITY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

asymmetric amination; branched aldehydes; primary amine

Indexed keywords

ALDEHYDE; DIAMINE DERIVATIVE; IMIDE;

AMINATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 84883872534     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22203     Document Type: Article

References (44)

1. Cheng L, Liu L, Wang D, Chen Y-J,. Highly enantioselective and organocatalytic α-amination of 2-oxindoles. Org Lett 2009; 11: 3874-3877.
2. Qian Z-Q, Zhou F, Du T-P, Wang B-L, Ding M, Zhao X-L, Zhou J,. Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of 3-substituted oxindoles. Chem Commun 2009; 6753-6755.
3. Saaby S, Bella M, Jørgensen KA,. Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of α-substituted α-cyanoacetates and β-dicarbonyl compounds. J Am Chem Soc 2004; 126: 8120-8121.
4. Poulsen TB, Alemparte C, Jørgensen KA,. Enantioselective organocatalytic allylic amination. J Am Chem Soc 2005; 127: 11614-11615.
5. Bold G, Fässler A, Capraro H-G, Cozens R, Klimkait T, Lazdins J, Mestan J, Poncioni B, Rösel J, Stover D, Blomley MT, Acemoglu F, Beck W, Boss E, Eschbach M, Hürlimann T, Masso E, Roussel S, Stoll KU, Wyss D, Lang M,. New aza-dipeptide analogues as potent and orally absorbed HIV-1 protease inhibitors: candidates for clinical development. J Med Chem 1998; 41: 3387.
6. Kraynack E, Lu P, Morgan BP, Morgans DJ, Muci A, Tochimoto T,. US patent US2009324511-A1.
7. Potluri RB, Venkata SH, Mulakala ARC, Kodali HP, Venkata SH, Kodali H,. WO2006137082-A1. Chem Abstr 2006; 146: 101038.
8. Kumar A, Soudagar SR, Mathur A, Gunjal ST, Panda NB, Jadhav DU, Madhur A,. EP1679072-A1. Chem Abstr 2006; 145: 124844.
9. Gennari C, Colombo L, Bertolini G,. Electrophilic azide transfer to chiral enolates. a general approach to the asymmetric synthesis of α-amino acids. J Am Chem Soc 1986; 108: 6394-6395.
10. Trimble LA, Vederas JC,. Amination of chiral enolates by dialkyl azodiformates. Synthesis of.alpha.-hydrazino acids and.alpha.-amino acids. J Am Chem Soc 1986; 108: 6397-6399.
11. Vogt H, Vanderheiden S, Bräse S,. The proline-catalysed asymmetric amination of α,α-disubstituted aldehydes. Synthesis of configurationally stable enantioenriched α-aminoaldehyes. Chem Commun 2003; 2448-2449.
12. Baumann T, Bächle M, Hartmann C, Bräse S,. Thermal effects in the organocatalytic asymmetric α-amination of disubstituted aldehydes with azodicarboxylates: a high-temperature organocatalysis. Eur J Org Chem 2008; 2207-2212.
13. Baumann T, Vogt H, Bräse S,. The proline-catalyzed asymmetric amination of branched aldehydes. Eur J Org Chem 2007; 266-282.
14. Suri JT, Steiner DD, Barbas CF III,. Organocatalytic enantioselective synthesis of metabotropic glutamate receptor ligands. Org Lett 2005; 7: 3885-3888.
15. Liu Y, Melgar-Fernández R, Juaristi E,. Enantioselective amination of α-phenyl-α-cyanoacetate catalyzed by chiral amines incorporating the α-phenylethyl auxiliary. J Org Chem 2007; 72: 1522-1525.
16. Fu J-Y, Xu X-Y, Li Y-C, Huang Q-C, Wang L-X,. Effective construction of quaternary stereocenters by highly enantioselective α-amination of branched aldehydes. Org Biomol Chem 2010; 8: 4524-4526.
17. Liu C, Zhu Q, Huang K-W, Lu YX,. Primary amine/CSA ion pair: a powerful catalytic system for the asymmetric enamine catalysis. Org Lett 2011; 13: 2638-2641.
18. Fu J-Y, Yang Q-C, Wang Q-L, Xu X-Y, Wang L-X,. Enantioselective α-amination of branched aldehydes promoted by simple chiral primary amino acids. J Org Chem 2011; 76: 4661-4664.
19. Huang H, Jacobsen E N,. Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst. J Am Chem Soc 2006; 128: 7170-7171.
20. Laloude MP, Chen Y, Jacobsen EN,. A chiral primary amine thiourea catalyst for the highly enantioselective direct conjugate addition of α,α-disubstituted aldehydes to nitroalkenes. Angew Chem Int Ed 2006; 45: 6366-6370.
21. Zhang X-J, Liu S-P, Li X-M, Yan M, Chan ASC,. Highly enantioselective conjugate addition of aldehydes to nitroolefins catalyzed by chiral bifunctional sulfamides. Chem Commun 2009; 833-835.
22. Zhu Q, Lu Y-X,. Chiral primary amine mediated conjugate addition of branched aldehydes to vinyl sulfone: asymmetric generation of quaternary carbon centers. Chem Commun 2010; 46: 2235-2237.
23. Uehara H, Barbas CF III,. Anti-selective asymmetric Michael reactions of aldehydes and nitroolefins catalyzed by a primary amine/thiourea. Angew Chem Int Ed 2009; 48: 9848-9852.
24. Wang YY, Yang HT, Yu J-P,. Highly enantioselective Biginelli reaction promoted by chiral bifunctional primary amine-thiourea catalysts: asymmetric synthesis of dihydropyrimidines. Adv Synth Catal 2009; 351: 3057-3062.
25. Deng L, Jacobsen EN,. A practical, highly enantioselective synthesis of the taxol side chain via asymmetric catalysis. J Org Chem 1992; 57: 4320-4323.
26. Jacobsen E N, Zhang W, Güler ML,. Electronic tuning of asymmetric catalysts. J Am Chem Soc 1991; 113: 6703-6704.
27. Jacobsen EN, Zhang W, Muci AR, Ecker JR, Deng L,. Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane. J Am Chem Soc 1991; 113: 7063-7064.
28. Trost BM, Van Vranken DL, Bingel C,. A modular approach for ligand design for asymmetric allylic alkylations via enantioselective palladium-catalyzed ionizations. J Am Chem Soc 1992; 114: 9327-9343.
29. Trost BM, Bunt RC,. On ligand design for catalytic outer sphere reactions: a simple asymmetric synthesis of vinylglycinol. Angew Chem Int Ed Engl 1996; 35: 99-102.
30. Trost BM, Toste FD,. Asymmetric O- and C-alkylation of phenols. J Am Chem Soc 1998; 120: 815-816.
31. Trost BM, Ariza X,. Catalytic asymmetric alkylation of nucleophiles: asymmetric synthesis of α-alkylated amino acids. Angew Chem Int Ed Engl 1997; 36: 2635-2637.
32. Trost BM, Radinov R, Grenzer EM,. Asymmetric alkylation of β-ketoesters. J Am Chem Soc 1997; 119: 7879-7880.
33. Okino T, Hoashi Y, Takemoto Y,. Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts. J Am Chem Soc 2003; 125: 12672-12673.
34. Bui T, Syed S, Barbas CF III,. Thiourea-catalyzed highly enantio- and diastereoselective additions of oxindoles to nitroolefins: application to the formal synthesis of (+)-physostigmine. J Am Chem Soc 2009; 131: 8758-8759.
35. Berkessel A, Mukherjee S, Müller TN, Cleemann F, Roland K, Brandenburg M, Neudörfl JM, Lex J,. Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones. Org Biomol Chem 2006; 4: 4319-4330.
36. Luo X-y, Wang L-l, Peng L, Bai J-f, Jia L-n, He G-y, Tian F, Xu X-y, Wang L-X,. Asymmetric double Michael reaction catalyzed by simple primary amine catalysts: a straightforward approach to construct spirocyclic oxindoles. Chin J Chem 2012; 30: 1185-1188.
37. Bai J-F, Guo Y-L, Peng L, Jia L-N, Xu X-Y, Wang L-X,. Enantioselective Diels-Alder reaction of anthrone and maleimide catalyzed by a simple chiral tertiary amine. Tetrahedron 2013; 69: 1229-1233.
38. Fu J-Y, Wang Q-L, Peng L, Gui Y-Y, Wang F, Tian F, Xu X-Y, Wang L-X,. Chiral α-Arylethanamines: an organocatalyst for the enantioselective α-amination of branched aldehydes. Eur J Org Chem 2013; 2864-2868.
39. Wang L-L, Bai J-F, Peng L, Qi L-W, Jia L-N, Guo Y-L, Luo X-Y, Xu X-Y, Wang L-X,. Organocatalytic stereocontrolled synthesis of 3,3'-pyrrolidinyl spirooxindoles by [3 + 2] annulation of isocyanoesters with methyleneindolinones. Chem Commun 2012; 48: 5175-5177.
40. Wang L-L, Peng L, Bai J-F, Jia L-N, Luo X-Y, Huang Q-C, Xu X-Y, Wang L-X,. A highly organocatalytic stereoselective double Michael reaction: efficient construction of optically enriched spirocyclic oxindoles. Chem Commun 2011; 47: 5593-5595.
41. Wang L-L, Peng L, Bai J-F, Huang Q-C, Xu X-Y, Wang L-X,. Highly organocatalytic asymmetric Michael-ketone aldol-dehydration domino reaction: straightforward approach to construct six-membered spirocyclic oxindoles. Chem Commun 2010; 46: 8064-8066.
42. Fu J-Y, Huang Q-C, Wang Q-W, Wang L-X, Xu X-Y,. Highly effective and enantioselective α-amination of aldehydes promoted by chiral proline amide-thiourea bifunctional catalysts. Tetrahedron Lett 2010; 51: 4870-4873.
43. Kaik M, Gawroński J,. Facile monoprotection of trans-1,2-diaminocyclohexane. Tetrahedron Asymmetry 2003; 14: 1559-1563.
44. Gawronski J, Gawronska K, Grajewski J, Kacprzak K, Rychlewska U,. Folding of aromatic oligoimides of trans-1,2-diaminocyclohexane. Chem Comm 2002; 582-583.