Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2005(12): 1923-1925
DOI: 10.1055/s-2005-869990
DOI: 10.1055/s-2005-869990
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of 3-Nitropropanol Homologues
Further Information
Received
20 December 2004
Publication Date:
13 July 2005 (online)
Publication History
Publication Date:
13 July 2005 (online)
Abstract
Several high yielding routes to oxygenated nitropropanes have been developed that include a palladium catalyzed nitro allylation of allylic carbonates, nitration of brominated compounds and a nitro aldol condensation/hydrogenation sequence.
Key words
nitroaldol - 3-nitropropanol - 3-nitropropanal - 3-nitropropanoic acid - ethyl glyoxylate
-
1a
Barrett AGM.Grabowski GG. Chem. Rev. 1986, 86: 751 -
1b
Ono N. The Nitro Group in Organic Synthesis Wiley-VCH; Weinheim, New York: 2001. -
1c
Berner OM.Tedeschi L.Enders D. Eur. J. Org. Chem. 2002, 1877 -
2a
Seebach D.Colvin EW.Lehr F.Weller T. Helv. Chim. Acta 1985, 68: 1592 -
2b
Brown BR. The Organic Chemistry of Aliphatic Nitrogen Compounds Oxford University; Oxford: 1994. p.443-469 -
2c
Seebach D.Colvin EW.Lehr F.Weller T. Chimia 1979, 33: 1 -
3a
The Chemistry of Amino, Nitro and Related Groups
Patai S. John Wiley & Sons; Chichester: 1996. -
3b
Rosini G.Ballini R. Synthesis 1988, 833 -
3c
Coombes RG. In Comprehensive Organic Chemistry Vol. 2:Barton DHR.Ollis WD.Sutherland IO. Pergamon Press; Oxford: 1979. p.303-382 -
4a
Vogel EM.Groger H.Shibasaki M. Angew. Chem. Int. Ed. 1999, 38: 1510 -
4b
Perekalin V.Lipina ES.Berestovitskaya VM.Efremov DA. Nitroalkenes Wiley; Chichester: 1994. -
4c
Ono N. The Nitro Group in Organic Synthesis Wiley-VCH; New York: 2001. -
5a
Sasai H.Tokunaga T.Watanabe S.Suzuki T.Itoh N.Shibasaki M. J. Org. Chem. 1995, 60: 7388 -
5b
Sasai H.Suzuki T.Arai S.Arai T.Shibasaki M. J. Am. Chem. Soc. 1992, 114: 4418 -
5c
Sasai H.Itoh N.Suzuki T.Shibasaki M. Tetrahedron Lett. 1993, 34: 855 -
5d
Funabashi K.Saida Y.Kanai M.Arai T.Susar H.Shibasaki M. Tetrahedron Lett. 1998, 39: 7557 -
6a
Trost BM.Crawley ML. Chem. Rev. 2003, 103: 2921 -
6b
Belda O.Moberg C. Acc. Chem. Res. 2004, 37: 159 -
6c
Kazmaier U. Curr. Org. Chem. 2003, 7: 317 -
6d
Trost BM. Chem. Pharm. Bull. 2002, 50: 1 -
7a For a related AgNO2 nitration see:
Kornblum N.Taub B.Ungnade HE. J. Am. Chem. Soc. 1954, 76: 3209 -
7b
Noland W.Hartman P. J. Am. Chem. Soc. 1954, 76: 3227 - 8
Luzzio FA. Tetrahedron 2001, 57: 915 ; and the references therein - 9
Amer I.Bravdo T.Blum J.Vollhardt KPC. Tetrahedron Lett. 1987, 28: 1321 - 10
Ranu BC.Chakraborty R. Tetrahedron 1992, 48: 5317 ; and references therein -
11a
Oehrlein R.Schwab W.Ehrler R.Jaeger V. Synthesis 1986, 535 -
11b
Griesser H.Ohrlein R.Schwab W.Ehrler R.Jager V. Org. Synth. 2000, 77: 236 - 12
Sellès P.Lett R. Tetrahedron Lett. 2002, 43: 4621 - 13
Hatakeyama S.Yoshida M.Esumi T.Iwabuchi Y.Irle H.Kawamoto T.Yamada H.Nishizawa M. Tetrahedron Lett. 1997, 38: 7887 -
14a
Bianco A.Melchioni C. Stud. Nat. Prod. Chem. 2002, 27: 103 -
14b
Unverzagt C. Angew. Chem., Int. Ed. Engl. 1993, 32: 1691 -
15a
Baer HH.Chiu S.-HL.Shields DC. Can. J. Chem. 1973, 51: 2828 -
15b
Baitinger WF.Schleyer PVR.Murty TSSR.Robinson L. Tetrahedron 1964, 20: 1635 - 16
Chou W.-C.Fotsch C.Wong C.-H. J. Org. Chem. 1995, 60: 2916 -
17a
Öhrlein R.Schwab W.Ehrler R.Jäger V. Synthesis 1988, 236 -
17b
Jung ME.Lowe JA.Lyster MA.Node M.Pfluger RW.Brown RW. Tetrahedron 1984, 40: 4751 - For examples of an enzymatic reduction of nitroalkenes to nitroalkanes see:
-
18a
Kamai Y.Inaba Y.Hayashi M.Tokitoh N. Tetrahedron Lett. 2001, 42: 3367 -
18b
Kawai Y.Inaba Y.Tokitoh N. Tetrahedron: Asymmetry 2001, 12: 309 -
18c
Ohta H.Ozaki K.Tsuchihashi G. Chem. Lett. 1987, 191 -
18d
Ohta H.Kobayashi N.Ozaki K. J. Org. Chem. 1989, 54: 1802 - 19
Czekelius C.Carreira EM. Org. Lett. 2004, 6: 4575 - 20
Jayakanthan K.Madhusudanan KP.Vankar Yashwant D. Tetrahedron 2004, 60: 397