RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2010(15): 2512-2514
DOI: 10.1055/s-0029-1218823
DOI: 10.1055/s-0029-1218823
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkA Short and Efficient Synthesis of (S)-(+)-2-(Hydroxymethyl)-6-piperidin-2-one
Weitere Informationen
Received
1 April 2010
Publikationsdatum:
18. Juni 2010 (online)
Publikationsverlauf
Publikationsdatum:
18. Juni 2010 (online)
Abstract
A concise synthesis of (S)-(+)-2-(hydroxymethyl)-6-piperidin-2-one is described that employs l-aspartic acid as chiral pool starting material and Wittig reaction as the key step.
Key words
Wittig reaction - amino acid - piperidone - l-aspartic acid - hydrogenation - pipecolate
- 1a
Hermitage SA.Moloney MG. Tetrahedron: Asymmetry 1994, 5: 1463 - 1b
Davies CE.Heightman TD.Hermitage SA.Moloney MG. Synth. Commun. 1996, 26: 687 - 1c
Ezquerra J.Pedregal C.Escribano A.Carreno MC.Ruano JLG. Tetrahedron Lett. 1995, 36: 3247 - 1d
Huang S.-B.Nelson JS.Weller DD. Synth. Commun. 1989, 3485 - 2
Hanessian S.Reinhold U.Gentile G. Angew. Chem. Int. Ed. 1997, 36: 1881 - 3
Huang S.-B.Nelson JS.Weller DD. J. Org. Chem. 1991, 56: 6007 - 4
Hodgkinson TJ.Shipman M. Synthesis 1998, 1141 - 5a
Pandey SK.Kumar P. Synlett 2007, 2894 - 5b
Pandey SK.Kumar P. Tetrahedron Lett. 2005, 46: 4091 - 5c
Cherian SK.Kumar P. Tetrahedron: Asymmetry 2007, 18: 982 - 5d
Kandula SV.Kumar P. Tetrahedron 2006, 62: 9942 - 5e
Kumar P.Bodas MS.
J. Org. Chem. 2005, 70: 360 - 5f
Bodas MS.Upadhyay PK.Kumar P. Tetrahedron Lett. 2004, 45: 987 - 5g
Upadhyay PK.Prasad R.Pandey M.Kumar P. Tetrahedron Lett. 2009, 50: 2440 - 6a
Fanning KN.Sutherland A. Tetrahedron Lett. 2007, 48: 8479 - 6b
Padron JM.Kokotos G.Martin T.Markidis T.Gibbons WA.Martin VS. Tetrahedron: Asymmetry 1998, 9: 3381