RSS-Feed abonnieren
PDF herunterladen
DOI: 10.1055/s-0030-1261163
Petasis Olefination in a Continuous-Flow Microwave Reactor: exo-Glycals from Sugar Lactones
Publikationsverlauf
Publikationsdatum:
10. August 2011 (online)
Abstract
An efficient Petasis olefination of sugar lactones under continuous-flow microwave conditions was developed. Their conversion into exo-glycals can be steered by adjusting the residence time and the concentration of the solution within the reactor. Applying a continuous-flow procedure, the reaction time can be shortened to less than three minutes, several hundred times shorter compared to values given in the literature for batch procedures. This setup is utilizable for a gram-scale synthesis of enol ethers and exo-glycals, in particular, such ones containing potentially (Lewis) acid sensitive acetalic protecting groups.
Key words
Petasis olefination - continuous-flow reactions - exo-glycals - sugar lactones - microwave support
- Supporting Information for this article is available online:
- Supporting Information (PDF)
- 1
Brand C.Rauch G.Zanoni M.Dittrich B.Werz DB. J. Org. Chem. 2009, 74: 8779 ; and literature cited thereinReference Ris Wihthout Link - 2
Woodward H.Smith N.Gallagher T. Synlett 2010, 869 - 3a
Maryanoff BE.Reitz AB. Chem. Rev. 1989, 89: 863Reference Ris Wihthout Link - 3b
Mikolajczyk M.Balczewski P. New Aspects in Phosphorous Chemistry II Springer; Berlin, Heidelberg: 2003. p.161-214Reference Ris Wihthout Link - 3c
Blakermore PR. J. Chem. Soc., Perkin Trans. 1 2002, 2563Reference Ris Wihthout Link - 3d
van Staden LF.Gravestock D.Ager D. J. Chem. Soc. Rev. 2002, 31: 195Reference Ris Wihthout Link - 4
Tebbe FN.Parshall GW.Reddy GS. J. Am. Chem. Soc. 1978, 100: 3611 - 5a
Petasis NA.Bzowej EI. J. Am. Chem. Soc. 1990, 112: 6392Reference Ris Wihthout Link - 5b
Petasis NA.Patane MA. Tetrahedron Lett. 1990, 31: 6799Reference Ris Wihthout Link - 5c
Petasis NA.Lu S.-P. Tetrahedron Lett. 1996, 37: 141Reference Ris Wihthout Link - 5d
Csuk R.Glänzer BI. Tetrahedron 1991, 47: 1655Reference Ris Wihthout Link - 5e
Hartley RC.McKiernan GJ.
J. Chem. Soc., Perkin Trans. 1 2002, 2763Reference Ris Wihthout Link - 5f
Hartley RC.Ji JF.Main CA.McKiernan GJ. Tetrahedron 2007, 63: 4825Reference Ris Wihthout Link - 6a
Payack JF.Hughes DL.Cai DW.Cottrell IF.Verhoeven TR. Org. Prep. Proced. Int. 1995, 27: 707Reference Ris Wihthout Link - 6b
Payack JF.Huffman MA.Cai DW.Hughes DL.Collins PC.Johnson BK.Cottrell IF.Tuma LD. Org. Process Res. Dev. 2004, 8: 256Reference Ris Wihthout Link - 7a
Hughes DL.Payack JF.Cai DW.Verhoeven TR.Reider PJ. Organometallics 1996, 15: 663Reference Ris Wihthout Link - 7b
Meurer EC.Santos LS.Pilli RA.Eberlin MN. Org. Lett. 2003, 5: 1391Reference Ris Wihthout Link - 8
Ley S.Gaunt MJ.Jessiman AS.Orsini P.Tanner HR.Hook DF. Org. Lett. 2003, 4819 - 9
Hartley RC.Adriaenssens LV. J. Org. Chem. 2007, 72: 10287 - 10
Gallagher T.Cook MJ.Declan WF. Tetrahedron Lett. 2005, 46: 297 - 11a
Kappe CO.Glasnov TN. Macromol. Rapid Commun. 2007, 28: 395Reference Ris Wihthout Link - 11b
Baxendale IR.Hayward JJ.Ley SV. Comb. Chem. High Throughput Screening 2007, 802Reference Ris Wihthout Link - 12
O’Brien M.Denton R.Ley SV. Synthesis 2011, 1157 - 13
Van Boom JH.Heskamp BM.Veeneman GH.van der Marel GA.van Boeckel CAA. Tetrahedron 1995, 51: 8397 - 14
Tanaka H.Kawai K.Fujiwara K.Murai A. Tetrahedron 2002, 58: 10017