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 2009(20): 3433-3438
DOI: 10.1055/s-0029-1216956
DOI: 10.1055/s-0029-1216956
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Erbium(III) Triflate is a Highly Efficient Catalyst for the Synthesis of β-Alkoxy Alcohols, 1,2-Diols and β-Hydroxy Sulfides by Ring Opening of Epoxides
Further Information
Received
25 May 2009
Publication Date:
21 August 2009 (online)
Publication History
Publication Date:
21 August 2009 (online)
Abstract
Chemo- and stereoselectivity in the ring-opening reaction of epoxides with erbium(III) triflate are described. Epoxides can be cleaved under neutral conditions with alcohols and thiols in the presence of catalytic amounts of Lewis acid, affording the corresponding β-alkoxy alcohols and β-hydroxy sulfides in high yields. In water, epoxide ring opening occurs to produce the corresponding diols in good yields
Key words
epoxides - Lewis acids - nucleophilic additions - ring opening - green chemistry
-
1a
Smith JG. Synthesis 1984, 629 -
1b
Luly JR.Yi N.Soderquist J.Stein H.Cohen J.Perun TJ.Plattner JJ. J. Med. Chem. 1987, 30: 1609 -
1c
Corey EJ.Cheng X.-M. The Logic of Chemical Synthesis Wiley; New York: 1989. -
1d
Jones RJ.Rapoport H. J. Org. Chem. 1990, 55: 1144 -
1e
Jaramillo C.Chiara JL.Martinlomas M. J. Org. Chem. 1994, 59: 3135 -
1f
Stead P.Marley H.Mahmoudian M.Webb G.Noble D.Ip YT.Piga E.Rossi T.Roberts S.Dawson MJ. Tetrahedron: Asymmetry 1996, 7: 2247 -
1g
Amantini D.Fringuelli F.Piermatti O.Tortoioli S.Vaccaro L. ARKIVOC 2002, (xi): 293 -
2a
Corey eJ.Clark DA.Goto G.Marfat A.Mioskowski C.Samuelsson B.Hammarstorm S. J. Am. Chem. Soc. 1980, 102: 3663 -
2b
Corey EJ.Clark DA.Goto G. Tetrahedron Lett. 1980, 21: 3143 -
3a
Jacobsen EN. Acc. Chem. Res. 2000, 33: 421 -
3b
Taylor SK. Tetrahedron 2000, 56: 1149 - See among others:
-
4a
Zhao PQ.Xu LW.Xia CG. Synlett 2004, 846 -
4b
Bartoli G.Bosco M.Carlone A.Locatelli M.Melchiorre P.Sambri L. Org. Lett. 2004, 6: 3973 -
4c
Mirkani V.Tangestaninejad S.Yadollahi B.Alipanah L. Catal. Lett. 2005, 101: 93 -
4d
Bartoli G.Bosco M.Carlone A.Locatelli M.Melchiorre P.Sambri L. Org. Lett. 2005, 7: 1983 -
4e
Ertürk E.Demir AS. ARKIVOC 2008, (ii): 160 - See among others:
-
5a
Tatarova LE.Korchagina DV.Volko KP.Salakhutdinov NF.Barkhash VA. Russ. J. Org. Chem. 2003, 39: 1076; Chem. Abstr. 2004, 140, 271015 -
5b
Fan RH.Hou XL. Tetrahedron Lett. 2003, 44: 4411 -
5c
Fogassy G.Pinel C.Gelbard G. Catal. Commun. 2009, 10: 557 - See among others:
-
6a
Bathia KA.Eash KJ.Leonard NM.Oswald MC.Mohan RS. Tetrahedron Lett. 2001, 42: 8129 -
6b
Serrano DP.van Grieken R.Melero JA.García A. Appl. Catal., A 2007, 319: 171 - See among others:
-
7a
Reddy MA.Surendra K.Bhanumathi N.Rao KR. Tetrahedron 2002, 58: 6003 -
7b
Boruwa J.Borah JC.Kalita B.Barua NC. Tetrahedron Lett. 2004, 45: 7355 -
7c
Salehi P.Dabiri M.Zolfigol MA.Fard MAB. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179: 1113 -
7d
Sengul ME.Menzek A.Sahin E.Arik M.Saracoglu N. Tetrahedron 2008, 64: 7289 -
7e
Cavdar H.Saracoglu N. Tetrahedron 2009, 65: 985 - See among others:
-
8a
Kantam ML.Jeyalakshmi KAK.Likhar PR. Catal. Lett. 2003, 89: 95 -
8b
Mirkhani V.Tangestaninejad S.Yadollahi B.Alipanah L. Tetrahedron 2003, 59: 8213 -
8c
Moghadam M.Tangestaninejad S.Mirkhani V.Shaibani R. Tetrahedron 2004, 60: 6105 -
8d
Kim BH.Piao F.Lee EJ.Kim JS.Jun YM.Lee BM. Bull. Korean Chem. Soc. 2004, 25: 881 -
8e
Firouzabadi H.Iranpoor N.Jafari AA.Makarem S. J. Mol. Catal. A: Chem. 2006, 250: 237 -
8f
Robinson MWC.Buckle R.Mabbett I.Grant GM.Graham AE. Tetrahedron Lett. 2007, 48: 4723 -
8g
Leitao AJL.Salvador JAR.Pinto RMA.Sà e Melo ML. Tetrahedron Lett. 2008, 49: 1694 - See among others:
-
9a
Fringuelli F.Pizzo F.Tortoioli S.Vaccaro L. Adv. Synth. Catal. 2002, 344 -
9b
Fringuelli F.Pizzo F.Tortoioli S.Vaccaro L. J. Org. Chem. 2003, 68: 8248 -
9c
Fringuelli F.Pizzo F.Tortoioli S.Vaccaro L. Green Chem. 2003, 5: 436 -
9d
Fan R.-H.Hou X.-L. J. Org. Chem. 2003, 68: 726 -
9e
Pironti V.Colonna S. Green Chem. 2005, 7: 43 -
9f
Wu J.Xia H.-G. Green Chem. 2005, 7: 708 -
9g
Reddy MS.Srinivas B.Sridhar R.Narender M.Rao KR. J. Mol. Catal. A: Chem. 2006, 255: 180 -
9h
Azizi N.Saidi MR. Catal. Commun. 2006, 7: 224 -
9i
Su W.Chen J.Wu H.Jin C. J. Org. Chem. 2007, 72: 4524 -
9j
Chakraborti SAK. J. Mol. Catal. A: Chem. 2007, 263: 137 -
9k
Gao P.Xu P.-F.Zhai H. Tetrahedron Lett. 2008, 49: 6536 -
9l
Yang M.-H.Yan G.-B.Zheng Y.-F. Tetrahedron Lett. 2008, 49: 6471 -
10a
Grieco PA. Organic Synthesis in Water Blackie Academic and Professional; London: 1998. -
10b
Tundo P.Ananstas PT. Green Chemistry: Challenging Perspectives Oxford University Press; Oxford: 1999. -
10c
Li C.-J.Chan T.-H. Comprehensive Organic Reactions in Aqueous Media 2nd ed.: Wiley; Hoboken: 2007. -
10d
Kobayashi S.Sugiura M.Kitagawa H.Lam WW.-L. Chem. Rev. 2002, 102: 2227 -
10e
Kobayashi S.Menabe K. Acc. Chem. Res. 2002, 35: 209 -
11a
Dalpozzo R.De Nino A.Maiuolo L.Nardi M.Procopio A.Tagarelli A. Synthesis 2004, 496 -
11b
Procopio A.Dalpozzo R.De Nino A.Maiuolo L.Nardi M.Romeo G. Org. Biomol. Chem. 2005, 3: 4129 -
11c
De Nino A.Dalpozzo R.Procopio A.Tagarelli A.Nardi M.Russo B. Synthesis 2006, 332 -
11d
Dalpozzo R.De Nino A.Nardi M.Russo B.Procopio A. Synthesis 2006, 1127 -
11e
Procopio A.Dalpozzo R.De Nino A.Nardi M.Oliverio M.Russo B. Synthesis 2006, 2608 -
11f
Dalpozzo R.De Nino A.Maiuolo L.Nardi M.Procopio A.Russo B.Tagarelli A. ARKIVOC 2006, (vi): 181 -
11g
Procopio A.Dalpozzo R.De Nino A.Maiuolo L.Nardi M.Oliverio M.Russo B. Carbohydr. Res. 2007, 342: 2125 -
11h
Procopio A.Gaspari M.Nardi M.Oliverio M.Romeo R. Tetrahedron Lett. 2008, 49: 1961 - 13
Procopio A.Dalpozzo R.De Nino A.Nardi M.Sindona G.Tagarelli A. Synlett 2004, 2633 - 14
Procopio A.Dalpozzo R.De Nino A.Maiuolo L.Nardi M.Russo B. Adv. Synth. Catal. 2005, 347: 1447 - 15
Dalpozzo R.De Nino A.Nardi M.Russo B.Procopio A. ARKIVOC 2006, (vi): 67 - 16
Procopio A.Gaspari M.Nardi M.Oliverio M.Rosati O. Tetrahedron Lett. 2008, 49: 2289 -
17a
Posner GH.Rogers DZ. J. Am. Chem. Soc. 1977, 99: 8214 -
17b
Otera J.Yoshinago Y.Hirakawa K. Tetrahedron Lett. 1985, 26: 3219 -
17c
Iranpoor N.Salehi P. Synthesis 1994, 1152 -
17d
Tokunaga M.Larrow JF.Kakiuchi F.Jacobsen EN. Science 1997, 277: 936 -
17e
Fringuelli F.Piermatti O.Pizzo F.Vaccaro L. J. Org. Chem. 1999, 64: 6094 -
17f
Iranpoor N.Adibi H. Bull. Chem. Soc. Jpn. 2000, 73: 675 -
17g
Schaus SE.Brandes BD.Larrow JF.Tokunaga M.Hansen KB.Gould AE.Furrow ME.Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 1307 -
17h
Schneider C.Sreekanth AR.Mai E. Angew. Chem. Int. Ed. 2004, 43: 5691 - 18
Iranpoor N.Mohammadpour Baltork I.Shiriny Zardaloo F. Tetrahedron 1991, 47: 9861 - 19
Yadav JS.Reddy BVS.Bayshya G. Chem. Lett. 2002, 906
References
A 0.1 M aqueous solution of Er(OTf)3 is only weakly acidic (pH ca. 5.9), and the aqueous layer from workup is even less acidic (pH ca. 6.6).