Electroreductive generation of (S)-(+)-N,N-dimethyl-2-(hydroxymethyl)- pyrrolidinium mercury compound for enantioselective synthesis of 2-amino-1-alkyl/aryl ethanols

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 45, Issue 12, 2006, Pages 2770-2772

  Yadav, Ashok K ^a   Manju, Meera ^a  

^a UNIVERSITY OF RAJASTHAN   (India)

Author keywords

Aminoalkyl aryl ethanols; Cathodic reduction; Enantioselective synthesis; Quaternary ammonium amalgams

Indexed keywords

EID: 33846287904     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. Roth H J & Kleemann A, Pharmaceutical Chemistry Vol. 1: Drug Synthesis, Ellis Horwood, 1988, p. 144.
2. Patil P N & Miller D D Trendelenburg, Pharmacol Rev 26, 1975, 323.
3. Britain R T, Jack D & Ritchie A C, Adv Drug Res, 5, 1970, 197.
4. Oguni N, Matsuda Y & Kaneko T, J Am Chem Soc, 110, 1983, 7877.
5. Howe R, Moore R H & Rao B S, J Med Chem. 16, 1973, 1020.
6. Takeda H, Tachinami T, Aburatani M, Takahashi H, Morimoto T & Achiwa K, Tetrahedron Lett, 30, 1980, 363.
7. Kitamura M, Okhuma T, Inoue S, Sayo N, Kumobayashi H, Akutagawa S, Ohta T, Takaya H & Noyori R, J Am Chem Soc 110, 1988, 629.
8. Cho Byung Tae & Chun Usung, Tetrahedron Asymm. 3, 1992, 341.
9. Yadav A K & Singh A, Synlett, 8, 2000, 1199.
10. Yadav A K & Singh A, Bull Chem Soc Jpn, 75, 2002, 587.
11. Yadav A K, Manju M & Chimpa P R, Tetrahedron Asymm, 14, 2003, 1079.
12. The α-aminoketones were prepared by reduction of aryl azidomethyl ketone, which was obtained by treatment of aryl halomethyl ketone with sodium azide, see Bretschneider H & Hormann H, Monatsch Chem. 84, 1953, 1021,
13. J was prepared by reported method; See Stolz, F, Chem Ber, 37, 1904.
14. Miyano S, Lu L D-L, Viti S M & Sharpless K B, J Org Chem, 50, 1985, 4350.
15. Raasch M S & Brode W R, J Am Chem Soc, 64, 1942, 1112.
16. Nabeya A, Shigemoto T & Iwakura Y, J Org Chem. 40, 1975, 3536.
17. Lyle G C, J Org Chem, 25, 1960, 1779.
18. Kariv-Miller E & Andruzzi R, J Electroanal Chem, 187, 1985, 175.
19. Kariv-Miller E & Vajtner Z, J Org Chem, 50, 1985, 1394.
20. Swartz J E, Mahachi T J & Kariv-Miller E, J Am Chem Soc, 110, 1988, 3622.
21. Lawin P B, Hutson A C & Kariv-Miller E, J Org Chem, 54, 1989, 526.
22. Gunderson E G, Svetlick V & Kariv-Miller E, J Electrochem Soc, 140, 1993, 1842.