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Synlett 2004(3): 564-571
DOI: 10.1055/s-2004-815435
DOI: 10.1055/s-2004-815435
NEWTOOLS
© Georg Thieme Verlag Stuttgart · New York
Vilsmeier-Haack Reagents. Novel Electrophiles for the One-Step Formylation of O-Silylated Ethers to O-Formates
Weitere Informationen
Received
30 October 2003
Publikationsdatum:
26. Januar 2004 (online)
Publikationsverlauf
Publikationsdatum:
26. Januar 2004 (online)
Abstract
Various O-silylated substrates were effectively converted in one-step to their corresponding O-formates using electrophilic racemic and homochiral Vilsmeier-Haack reagents. Reactivity trends of these transformations were examined that, specifically, emphasized their synthetic potential.
Key words
Vilsmeier-Haack complexes - deprotection of O-silyl ethers - one-step deprotection - preparation of O-formates - formyl glycosides
- 1
Greene TW.Wuts PGM. Protective Groups in Organic Synthesis 3rd Ed.: John Wiley and Sons Inc.; New York: 1999. - 2
Kocie PJ. Protecting Groups Georg Thieme Verlag; Stuttgart: 1994.ski - 3
Prakash C.Saleh S.Blair IA. Tetrahedron Lett. 1994, 35: 7565 - 4
Maiti G.Roy SC. Tetrahedron Lett. 1997, 38: 495 -
5a
Kim S.Lee WJ. Synth. Commun. 1986, 16: 659 -
5b
Oriyama T.Oda M.Gono J.Koga G. Tetrahedron Lett. 1994, 35: 2027 -
5c
Ganem B.Small RV. J. Org. Chem. 1974, 39: 3728 -
5d
Oriyama T.Noda K.Yatabe K. Synlett 1997, 701 -
5e
Chandra KL.Saravanan P.Singh VK. Tetrahedron Lett. 2001, 42: 5309 -
5f
Sharma GVM.Mahalingam AK.Nagarajan M.Ilangovan A.Radhakrishna P. Synlett 1999, 1200 -
5g
Reddy CS.Smitha G.Chandrasekhar S. Tetrahedron Lett. 2003, 44: 4693 - 6
Saunders DG. Synthesis 1988, 377 - 7
Suzuki T.Oriyama T. Synthesis 2001, 555 - 8
Marson CM. Tetrahedron 1992, 48: 3659 - 9
Marson CM.Giles PR. Synthesis Using Vilsmeier Reagents CRC Press; Boca Raton: 1994. - 10
Koeller S.Lellouche J.-P. Tetrahedron Lett. 1999, 40: 7043 - 11
Lellouche J.-P.Koeller S. J. Org. Chem. 2001, 66: 693 - 12
Martinez AG.Alvarez RM.Barcina JO.de la Moya Cerero S.Vilar ET.Fraile AG.Hanack M.Subramanian LR. J. Chem. Soc., Chem. Commun. 1990, 1571 - 13
Ramesh NG.Balasubramanian KK. Tetrahedron Lett. 1991, 32: 3875 - 14
Lide DR. Handbook of Chemistry and Physics 8th Ed.: CRC Press; Boca Raton: 1997. p.9/667 - 15
Friesen RW.Danishefsky SJ. J. Am. Chem. Soc. 1989, 11: 6656 - 16
Danishefsky SJ.Bilodeau MT. Angew. Chem., Int. Ed. Engl. 1996, 35: 1381 - 17
Cohen Y. MSc Thesis Bar-Ilan University; Ramat-Gan Israel: 2002. -
18a
Bols M.Skrydstrup T. Chem. Rev. 1995, 95: 1253 -
18b
Fensterbank L.Malacria M.Sieburth S. Synthesis 1997, 813 -
18c
Gauthier DR.Zandi KS.Shea KJ. Tetrahedron 1998, 54: 228 - 19
Cohen Y.Kotlyar V.Koeller S.Lellouche J.-P. Synlett 2001, 1543 - 20
Chmurski K.Defaye J. Tetrahedron Lett. 1997, 42: 7365 -
21a
Khan AR.D’Souza VT. J. Org. Chem. 1994, 59: 7492 -
21b
Benazza M.Massoui M.Uzan R.Demailly G. Carbohydr. Res 1995, 275: 421 -
21c
Benazza M.Beaupere D.Uzan R.Demailly G. Carbohydr. Res. 1991, 218: 75 - 22
Djuric SW. J. Org. Chem. 1984, 49: 1311 - 23
Hodosi G.Podanyi B.Kuszmann J. Carbohydr. Res. 1992, 230: 327 -
24a
Gorin BI.Riopelle RJ.Thatcher GRJ. Tetrahedron Lett. 1996, 37: 4647 -
24b
Baer HH.Berenguel AV.Shu YY. Carbohydr. Res. 1992, 228: 307 -
24c
Gadelle A.Defaye J. Angew. Chem. Int. Ed. Engl. 1991, 30: 78 - 25
Barluenga J.Campos PJ.Gonzalez-Nunez E.Asensio G. Synthesis 1985, 426 - 26
De Luca L.Giacomelli G.Porcheddu A. Org. Lett. 2002, 4: 553