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-00000083.xml
Synlett 2005(10): 1615-1617
DOI: 10.1055/s-2005-869867
DOI: 10.1055/s-2005-869867
LETTER
© Georg Thieme Verlag Stuttgart · New York
The Preparation of Enantiomerically Pure 3,4-Epoxy-1-butene and 3-Butene-1,2-diol
Weitere Informationen
Received
11 March 2005
Publikationsdatum:
07. Juni 2005 (online)
Publikationsverlauf
Publikationsdatum:
07. Juni 2005 (online)
Abstract
Single enantiomer 2-hydroxy-3-butenyl tosylate is a key precursor for single enantiomer 3,4-epoxy-1-butene and 3-butene-1,2-diol. The epoxide results from ring-closure of the hydroxy-tosylate while the diol is obtained through the intermediacy of the corresponding cyclic carbonate. This latter sequence avoids the loss of enantiomeric purity observed through direct hydrolysis.
Key words
epoxides - asymmetric synthesis - chirality - diols - nucleophiles
-
1a
Kozikowski AP.Ghosh AK. J. Am. Chem. Soc. 1982, 104: 5788 -
1b
Kozikowski AP.Ghosh AK. J. Org. Chem. 1984, 49: 2762 - 2
Walkup RD.Cunningham RT. Tetrahedron Lett. 1987, 28: 4019 -
3a
Rama Rao AV.Reddy ER.Joshi BV.Yadav JS. Tetrahedron Lett. 1987, 28: 6497 -
3b
Rama Rao AV.Bose DS.Gurjar MK.Ravindranathan T. Tetrahedron 1989, 45: 7031 - 4
Gurjar MK.Devi NR. Tetrahedron: Asymmetry 1994, 5: 755 - 5
Bergmeier SC.Stanchina DM. J. Org. Chem. 1999, 64: 2852 - 6
Maeda M.Okazaki F.Murayama M.Tachibana Y.Aoyagi Y.Ohta A. Chem. Pharm. Bull. 1997, 45: 962 - 7
Ohgiya T.Nishiyama S. Heterocycles 2004, 63: 2349 -
8a
Baer E.Fischer HO. J. Biol. Chem. 1939, 128: 463 -
8b
Crawford RJ.Lutener SB.Cockcroft RD. Can. J. Chem. 1976, 54: 3364 -
9a
Jung ME.Shaw TJ. J. Am. Chem. Soc. 1980, 102: 6304 -
9b
Marco JL.Rodriguez B. Tetrahedron Lett. 1988, 29: 1997 -
9c
Takano S.Numata H.Ogasawara K. Heterocycles 1982, 19: 327 -
9d
Hubschwerlen C. Synthesis 1986, 962 - 10
Howes DA.Brookes MH.Coates D.Golding BT.Hudson AT. J. Chem. Res., Synop. 1983, 9 ; J. Chem. Res., Miniprint 1983, 217 -
11a
Tokunaga M.Larrow JF.Kakiuchi F.Jacobsen EN. Science 1997, 277: 936 -
11b
Schaus SE.Brandes BD.Larrow JF.Tokunaga M.Hansen KB.Gould AE.Furrow ME.Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 1307 -
12a
Trost BM.McEachern EJ. J. Am. Chem. Soc. 1999, 121: 8649 -
12b
Cheeseman N.Fox M.Jackson M.Lennon IC.Meek G. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5396 - 13
Boaz NW.Zimmerman RL. Tetrahedron: Asymmetry 1994, 5: 153 - 14
Neagu C.Hase T. Tetrahedron Lett. 1993, 34: 1629 - 15
Boaz NW. Tetrahedron: Asymmetry 1995, 6: 15 -
16a
Cardillo G.Orena M.Porzi G.Sandri S. Synthesis 1981, 793 -
16b
Myers AG.Widdowson KL. Tetrahedron Lett. 1988, 29: 6389 - 17
Boaz NW. inventors; US Patent No. 5312950.