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Synlett 2003(5): 0667-0670
DOI: 10.1055/s-2003-38363
DOI: 10.1055/s-2003-38363
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York
Unsaturated Sultones from Unsaturated Sulfonates: Synthesis by Ring-Closing Metathesis and Reactivity
Further Information
Received
22 January 2003
Publication Date:
28 March 2003 (online)
Publication History
Publication Date:
28 March 2003 (online)
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Abstract
Unsaturated sultones can be efficiently synthesized by ring-closing metathesis of the corresponding unsaturated sulfonates derived from primary and secondary alkenols or alkynols. These compounds can be converted to 1,3-dienes under basic conditions in the presence of carbenoid species.
Key words
sulfonate - cyclization - metathesis - sultone - metalation - carbenoid - diene
- Reviews on olefin metathesis:
-
1a
Schuster M.Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36: 2036 -
1b
Armstrong SK. J. Chem. Soc., Perkin Trans. 1 1998, 371 -
1c
Grubbs RH.Chang RH. Tetrahedron 1998, 54: 4413 -
1d
Phillips AJ.Abell AD. Aldrichimica Acta 1999, 32: 75 -
1e
Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3013 -
1f
Trnka TM.Grubbs RH. Acc. Chem. Res. 2001, 34: 18 - 2
Schrock RH.Murcizek JS.Bazan GC.Robbins J.DiMare M.O’Regan M. J. Am. Chem. Soc. 1990, 112: 3875 -
3a
Grubbs RH.Schwab RH.France MB.Ziller JW. Angew. Chem., Int. Ed. Engl. 1995, 34: 2039 -
3b
Scholl M.Ding S.Lee CW.Grubbs RH. Org. Lett. 1999, 1: 953 - 4
Yet L. Chem. Rev. 2000, 100: 2963 -
5a
Armstrong SK.Christie BA. Tetrahedron Lett. 1996, 37: 9373 -
5b
Barrett AGM.Baugh SPD.Gibson VC.Giles MR.Marshall EL.Procopiou PA. Chem. Commun. 1997, 155 -
5c
Shon Y.-S.Lee TR. Tetrahedron Lett. 1997, 38: 1283 -
6a
Hanson PR.Probst DA.Robinson RE.Yau M. Tetrahedron Lett. 1999, 40: 4761 -
6b
Brown RCD.Castro JL.Moriggi J.-D. Tetrahedron Lett. 2000, 41: 3681 -
6c
Lane C.Snieckus V. Synlett 2000, 1294 -
6d
Long DD.Termin AP. Tetrahedron Lett. 2000, 41: 6743 -
6e
Wanner J.Harned AM.Probst DA.Poon KWC.Klein TA.Snelgrove KA.Hanson PR. Tetrahedron Lett. 2002, 43: 917 -
7a
Miller JF.Termin A.Koch K.Piscopio AD. J. Org. Chem. 1998, 63: 3158 -
7b
Paquette LA.Fabris F.Tae J.Gallucci JC.Hofferberth JE. J. Am. Chem. Soc. 2000, 122: 3391 -
7c
Yao Q. Org. Lett. 2002, 4: 427 - 8
Karsch S.Schwab P.Metz P. Synlett 2002, 2019 -
9a
Truce WE.Norell JR. J. Am. Chem. Soc. 1963, 85: 3231 -
9b
King JF.Harding DRK. J. Am. Chem. Soc. 1976, 98: 3312 -
9c
Bonini BF.Kemperman G.Willems STH.Fochi M.Mazzanti G.Zwanenburg B. Synlett 1998, 1411 -
10a
Metz P.Fleicher B. Synlett 1993, 399 -
10b
Metz P.Fleischer B.Fröhlich R. Tetrahedron 1995, 51: 711 - Reviews on sultones chemistry:
-
11a
Roberts DW.Williams DL. Tetrahedron 1987, 43: 1027 -
11b
Burglass AJ.Tillett JG. In The Chemistry of Sulfonic Acids, Esters and their DerivativesPataï S.Rappoport Z. Wiley; New York: 1991. p.789-878 -
11c
Metz P. J. Prakt. Chem. 1998, 340: 1 - 12
Durst T.du Manoir J. Can. J. Chem. 1969, 47: 1230 - 13
Zoller U. In The Synthesis of Sulphones, Sulphoxides and Cyclic SulphidesPataï S.Rappoport Z. Wiley; New York: 1994. p.389-482 -
14a
Charreau P.Julia M.Verpeaux J.-N. J. Organomet. Chem. 1989, 379: 201 -
14b
Charreaux P.Julia M.Verpeaux J.-N. Bull. Soc. Chim. Fr. 1990, 127: 275 -
14c
Plietker B.Metz P. Tetrahedron Lett. 1998, 39: 7827 -
14d
Plietker B.Seng D.Fröhlich R.Metz P. Eur. J. Org. Chem. 2001, 3669