Double bond isomerization/enantioselective aza-petasis-ferrier rearrangement sequence as an efficient entry to anti- and enantioenriched β-Amino Aldehydes

Journal of the American Chemical Society

Volumn 131, Issue 18, 2009, Pages 6354-6355

  Terada, Masahiro ^a   Toda, Yasunori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; ALDEHYDES; AMINES; CATALYSIS; ETHERS; PHOSPHORIC ACID;

ALIPHATIC SUBSTITUENTS; ALLYL ETHERS; AMINO ALDEHYDES; CATALYTIC REACTIONS; DOUBLE BONDS; ENANTIOSELECTIVE SYNTHESIS; FERRIER REARRANGEMENT; NI COMPLEXES; VINYL ETHERS;

AMINATION;

ALDEHYDE; ALKENE; ETHER DERIVATIVE; VINYL DERIVATIVE; VINYL ETHER;

CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; ALKENES; ETHERS; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 69949180302     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja902202g     Document Type: Article

References (19)

1. Yang, J. W.; Stadler, M.; List, B. Angew. Chem., Int. Ed. 2007, 46, 609-611.
2. Zhang, H.; Mitsumori, S.; Utsumi, N.; Imai, M.; Garcia-Delgado, N.; Mifsud, M.; Albertshofer, K.; Cheong, P. H.-Y.; Houk, K. N.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2008, 130, 875-886.
3. Kano, T.; Yamaguchi, Y.; Maruoka, K. Angew. Chem., Int. Ed. 2009, 48, 1838-1840, and references cited therein.
4. Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83-85.
5. Arenz, T.; Frauenrath, H.; Raabe, G.; Zorn, M. Liebigs Ann. Chem. 1994, 931-942.
6. Tayama, E.; Otoyama, S.; Isaka, W. Chem. Commun. 2008, 4216-4218.
7. For recent Reviews, see: Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713-5743.
8. Akiyama, T. Chem. Rev. 2007, 107, 5744-5758.
9. Terada, M. Chem. Commun. 2008, 4097-4112.
10. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566-1568.
11. Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356-5357.
12. Activation of hemiaminal ethers, see: Terada, M.; Machioka, K.; Sorimachi, K. Angew. Chem., Int. Ed. 2009, 48, 2553-2556.
13. Geometrical isomers of 2a were separated by HPLC.
14. Wille, A.; Tomm, S.; Frauenrath, H. Synthesis 1998, 305-308.
15. Yamamoto, Y.; Kurihara, K.; Yamada, A.; Takahashi, M.; Takahashi, Y.; Miyaura, N. Tetrahedron 2003, 59, 537-542.
16. See Supporting Information for details of nickel complex-catalyzed isomerization. Isomerization of hemiaminal crotyl ether provided the corresponding vinyl ether in low yield under the optimal conditions.
17. After isomerization was completed, the reaction mixture was quenched by a few drops of hydrogen peroxide to oxidize the phosphine ligand. The mixture was then passed through a short column to remove nickel salts and the phosphine oxide. Exchange of the solvent from THF to AcOEt or acetone allowed subsequent rearrangement without the need for purification and separation of the geometrical isomers of 2.
18. Mohr, J. T.; Ebner, D. C.; Stoltz, B. M. Org. Biomol. Chem. 2007, 5, 3571-3576.
19. Partial epimerization at the stereogenic center of 2a cannot be ruled out.