Synlett, Table of Contents NEWTOOLS © Georg Thieme Verlag Stuttgart · New York Vilsmeier-Haack Reagents. Novel Electrophiles for the One-Step Formylation of O-Silylated Ethers to O-Formates Jean-Paul Lellouche*, Vadim KotlyarDepartment of Chemistry, Bar-Ilan University, Ramat-Gan, 52900 IsraelFax: +972(3)5351250; e-Mail: lellouj@mail.biu.ac.il; Recommend Article Abstract Buy Article All articles of this category 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 Full Text References References 1 Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd Ed.: John Wiley and Sons Inc.; New York: 1999. 2 Kocieski PJ. Protecting Groups Georg Thieme Verlag; Stuttgart: 1994. 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