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DOI: 10.1055/s-0030-1259951
Diethyl Tartrate
Publication History
Publication Date:
18 April 2011 (online)
Introduction
Diethyl tartrate (DET) is a clear colorless slightly viscous liquid. It is the diethyl ester of tartaric acid, which is one of the most important α-hydroxy acids and originates from the chiral pool. l-DET (CAS: 87-91-2) and d-DET (CAS: 13811-71-7) are abundant and commercially available at low and moderate cost, respectively.
Diethyl tartrate has a wide range of applications in organic synthesis including precursors for chiral catalysts [¹] and auxiliaries. [²] The desired stereoselectivity is tunable upon use of the corresponding enantiomer of diethyl tartrate. It was efficiently applied as a scaffold for the enantioselective synthesis of biomolecules. [³] In addition, it has been employed as a chiral resolving reagent. [4]
- 1
Elston CL.Jackson RFW.MacDonald SJF.Murray PJ. Angew. Chem. Int. Ed. 1997, 36: 410 ; Angew. Chem. 1997, 109: 379 -
2a
Arai I.Mori A.Yamamoto H. J. Am. Chem. Soc. 1985, 107: 8254 -
2b
Mori A.Arai I.Yamamoto H. Tetrahedron 1986, 42: 6447 -
3a
Fernandes RA.Dhall A.Ingle AB. Tetrahedron Lett. 2009, 50: 5903 -
3b
Calderón F.Doyagüez EG.Fernández-Mayorlas A. J. Org. Chem. 2006, 71: 6258 - 4
Bortolini O.Di Furia F.Licini G.Modena G.Rossi M. Tetrahedron Lett. 1986, 27: 6257 - 5
Katsuki T.Sharpless KB. J. Am. Chem. Soc. 1980, 102: 5974 - 6
Finn MG.Sharpless KB. J. Am. Chem. Soc. 1991, 113: 113 - 7
Gao Y.Hanson RM.Klunder JM.Ko SY.Masamune H.Sharpless KB. J. Am. Chem. Soc. 1987, 109: 5765 -
8a
Pitchen P.Kagan HB. Tetrahedron Lett. 1984, 25: 1049 -
8b
Pitchen P.Dunach E.Deshmukh MN.Kagan HB. J. Am. Chem. Soc. 1984, 106: 8188 - 9
Yasuda M.Shimizu K.Yamasaki S.Baba A. Org. Biomol. Chem. 2008, 6: 2790 - 10
De B B.Sivaram S.Dhal PK. Polymer 1992, 33: 1756 - 11
Spengler J.Pelay M.Tulla-Puche J.Albericio F. Amino Acids 2010, 39: 161 - 12
Weng J.Li Y.-B.Wang R.-B.Li F.-Q.Liu C.Chan ASC.Lu G. J. Org. Chem. 2010, 75: 3125 - 13
von Itzstein M.Wu W.-Y.Kok GB.Pegg MS.Daysan JC.Jin B.Phan TV.Smythe ML.White HF.Oliver SW.Colman PM.Varghese JN.Ryan DM.Woods JM.Bethell RC.Hotham VJ.Cameron JM.Penn CR. Nature 1993, 363: 418 - 14
Palomo C.Aizpurua JM.Urchegui R.Garcia JM.
J. Chem. Soc., Chem. Commun. 1995, 2327 -
15a
Jayaraman M.Manhas MS.Bose AK. Tetrahedron Lett. 1997, 38: 709 -
15b
Tiwari DK.Gumaste VK.Deshmukh ARAS. Synthesis 2006, 115 - 16
Chincholkar PM.Puranik VG.Deshmukh ARAS. Synlett 2007, 2242