Synlett, Inhaltsverzeichnis NEWTOOLS© Georg Thieme Verlag Stuttgart · New YorkVilsmeier-Haack Reagents. Novel Electrophiles for the One-Step Formylation of O-Silylated Ethers to O-FormatesJean-Paul Lellouche*, Vadim KotlyarDepartment of Chemistry, Bar-Ilan University, Ramat-Gan, 52900 IsraelFax: +972(3)5351250; e-Mail: lellouj@mail.biu.ac.il; Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) 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 Volltext Referenzen References <A NAME="RT02003ST-1">1</A> Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd Ed.: John Wiley and Sons Inc.; New York: 1999. <A NAME="RT02003ST-2">2</A> Kocie ski PJ. Protecting Groups Georg Thieme Verlag; Stuttgart: 1994. <A NAME="RT02003ST-3">3</A> Prakash C. Saleh S. Blair IA. Tetrahedron Lett. 1994, 35: 7565 <A NAME="RT02003ST-4">4</A> Maiti G. Roy SC. Tetrahedron Lett. 1997, 38: 495 <A NAME="RT02003ST-5A">5a</A> Kim S. Lee WJ. Synth. Commun. 1986, 16: 659 <A NAME="RT02003ST-5B">5b</A> Oriyama T. Oda M. Gono J. Koga G. Tetrahedron Lett. 1994, 35: 2027 <A NAME="RT02003ST-5C">5c</A> Ganem B. Small RV. J. Org. Chem. 1974, 39: 3728 <A NAME="RT02003ST-5D">5d</A> Oriyama T. Noda K. Yatabe K. Synlett 1997, 701 <A NAME="RT02003ST-5E">5e</A> Chandra KL. Saravanan P. Singh VK. Tetrahedron Lett. 2001, 42: 5309 <A NAME="RT02003ST-5F">5f</A> Sharma GVM. Mahalingam AK. Nagarajan M. Ilangovan A. Radhakrishna P. Synlett 1999, 1200 <A NAME="RT02003ST-5G">5g</A> Reddy CS. Smitha G. Chandrasekhar S. Tetrahedron Lett. 2003, 44: 4693 <A NAME="RT02003ST-6">6</A> Saunders DG. Synthesis 1988, 377 <A NAME="RT02003ST-7">7</A> Suzuki T. Oriyama T. Synthesis 2001, 555 <A NAME="RT02003ST-8">8</A> Marson CM. Tetrahedron 1992, 48: 3659 <A NAME="RT02003ST-9">9</A> Marson CM. Giles PR. Synthesis Using Vilsmeier Reagents CRC Press; Boca Raton: 1994. <A NAME="RT02003ST-10">10</A> Koeller S. Lellouche J.-P. Tetrahedron Lett. 1999, 40: 7043 <A NAME="RT02003ST-11">11</A> Lellouche J.-P. Koeller S. J. Org. Chem. 2001, 66: 693 <A NAME="RT02003ST-12">12</A> 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 <A NAME="RT02003ST-13">13</A> Ramesh NG. Balasubramanian KK. Tetrahedron Lett. 1991, 32: 3875 <A NAME="RT02003ST-14">14</A> Lide DR. Handbook of Chemistry and Physics 8th Ed.: CRC Press; Boca Raton: 1997. p.9/667 <A NAME="RT02003ST-15">15</A> Friesen RW. Danishefsky SJ. J. Am. Chem. Soc. 1989, 11: 6656 <A NAME="RT02003ST-16">16</A> Danishefsky SJ. Bilodeau MT. Angew. Chem., Int. Ed. Engl. 1996, 35: 1381 <A NAME="RT02003ST-17">17</A> Cohen Y. MSc Thesis Bar-Ilan University; Ramat-Gan Israel: 2002. <A NAME="RT02003ST-18A">18a</A> Bols M. Skrydstrup T. Chem. Rev. 1995, 95: 1253 <A NAME="RT02003ST-18B">18b</A> Fensterbank L. Malacria M. Sieburth S. Synthesis 1997, 813 <A NAME="RT02003ST-18C">18c</A> Gauthier DR. Zandi KS. Shea KJ. Tetrahedron 1998, 54: 228 <A NAME="RT02003ST-19">19</A> Cohen Y. Kotlyar V. Koeller S. Lellouche J.-P. Synlett 2001, 1543 <A NAME="RT02003ST-20">20</A> Chmurski K. Defaye J. Tetrahedron Lett. 1997, 42: 7365 <A NAME="RT02003ST-21A">21a</A> Khan AR. D’Souza VT. J. Org. Chem. 1994, 59: 7492 <A NAME="RT02003ST-21B">21b</A> Benazza M. Massoui M. Uzan R. Demailly G. Carbohydr. Res 1995, 275: 421 <A NAME="RT02003ST-21C">21c</A> Benazza M. Beaupere D. Uzan R. Demailly G. Carbohydr. Res. 1991, 218: 75 <A NAME="RT02003ST-22">22</A> Djuric SW. J. Org. Chem. 1984, 49: 1311 <A NAME="RT02003ST-23">23</A> Hodosi G. Podanyi B. Kuszmann J. Carbohydr. Res. 1992, 230: 327 <A NAME="RT02003ST-24A">24a</A> Gorin BI. Riopelle RJ. Thatcher GRJ. Tetrahedron Lett. 1996, 37: 4647 <A NAME="RT02003ST-24B">24b</A> Baer HH. Berenguel AV. Shu YY. Carbohydr. Res. 1992, 228: 307 <A NAME="RT02003ST-24C">24c</A> Gadelle A. Defaye J. Angew. Chem. Int. Ed. Engl. 1991, 30: 78 <A NAME="RT02003ST-25">25</A> Barluenga J. Campos PJ. Gonzalez-Nunez E. Asensio G. Synthesis 1985, 426 <A NAME="RT02003ST-26">26</A> De Luca L. Giacomelli G. Porcheddu A. Org. Lett. 2002, 4: 553