Catalytic Staudinger-Vilarrasa Reaction for the Direct Ligation of Carboxylic Acids and AzidesCitation formats

  • Authors:
  • J. Bures
  • M. Martin
  • F. Urpi
  • J. Vilarrasa

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Catalytic Staudinger-Vilarrasa Reaction for the Direct Ligation of Carboxylic Acids and Azides : Journal of Organic Chemistry. / Bures, J.; Martin, M.; Urpi, F.; Vilarrasa, J.

In: The Journal of organic chemistry, Vol. 74, 2009, p. 2203-2206.

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Bures, J. ; Martin, M. ; Urpi, F. ; Vilarrasa, J. / Catalytic Staudinger-Vilarrasa Reaction for the Direct Ligation of Carboxylic Acids and Azides : Journal of Organic Chemistry. In: The Journal of organic chemistry. 2009 ; Vol. 74. pp. 2203-2206.

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@article{3e37c96b5f5f4818a981e806ed3161aa,
title = "Catalytic Staudinger-Vilarrasa Reaction for the Direct Ligation of Carboxylic Acids and Azides: Journal of Organic Chemistry",
abstract = "2,2'-Dipyridyl diselenide (PySeSePy) is the catalyst or activator of choice for the direct reaction of carboxylic acids with azides and trimethylphosphine at room temperature. The mechanism of the process, which is not an aza-Wittig reaction, has been elucidated.",
keywords = "native chemical ligation oxidation-reduction condensation aza-wittig reaction one-pot preparation 2 redox reactions peptide synthesis synthetic tricks natural-products puromycin analogs glycosyl azides",
author = "J. Bures and M. Martin and F. Urpi and J. Vilarrasa",
note = "M1 - 5 ISI Document Delivery No.: 415GG Times Cited: 4 Cited Reference Count: 61 Cited References: AFONSO CAM, 1995, TETRAHEDRON LETT, V36, P8857 ALAJARIN M, 1999, J CHEM SOC PERK T 2, P1811 ARIZA X, 1998, TETRAHEDRON LETT, V39, P9101 ARIZA X, 1999, TETRAHEDRON LETT, V40, P7515 ARIZA X, 2001, TETRAHEDRON LETT, V42, P4995 BACHI MD, 1979, J ORG CHEM, V44, P4393 BARLUENGA J, 1990, J CHEM SOC P1, P2193 BASKIN JM, 2007, QSAR COMB SCI, V26, P1211, DOI 10.1002/qsar.200740086 BLANCOCANOSA JB, 2008, ANGEW CHEM INT EDIT, V47, P6851, DOI 10.1002/anie.200705471 BOSCH I, 1993, TETRAHEDRON LETT, V34, P4671 BOSCH I, 1995, J CHEM SOC CHEM 0107, P91 BOSCH I, 1996, J ORG CHEM, V61, P5638 CHAPUIS H, 2006, TETRAHEDRON, V62, P12108, DOI 10.1016/j.tet.2006.09.045 CHAPUIS H, 2008, TETRAHEDRON LETT, V49, P6838, DOI 10.1016/j.tetlet.2008.09.078 CHARAFEDDINE A, 2007, CHEM-EUR J, V13, P5566, DOI 10.1002/chem.200700058 CHARAFEDDINE A, 2007, ORG LETT, V9, P2787, DOI 10.1021/ol070818q COREY EJ, 1974, J AM CHEM SOC, V96, P5614 DAVID O, 2003, ANGEW CHEM INT EDIT, V42, P4373, DOI 10.1002/anie.200351930 DAWSON P, 2007, CHEM BIOL, V2, P567 EGUCHI S, 2005, ARKIVOC 2, P98 FRESNEDA PM, 2004, SYNLETT 0105, P1, DOI 10.1055/s-2003-43338 GARCIA J, 1984, TETRAHEDRON LETT, V25, P4841 GARCIA J, 1986, TETRAHEDRON LETT, V27, P639 GARCIA J, 1986, THESIS U BARCELONA GHOSH SK, 1992, TETRAHEDRON LETT, V33, P805 GHOSH SK, 1996, B CHEM SOC JPN, V69, P1705 HAASE C, 2008, ANGEW CHEM INT EDIT, V47, P6807, DOI 10.1002/anie.200801590 HACKENBERGER CPR, 2008, ANGEW CHEM INT EDIT, V47, P10030, DOI 10.1002/anie.200801313 HICKEY DMB, 1984, CHEM COMMUN, P776 HIEBL J, 1988, LIEBIGS ANN CHEM, P765 HORNER L, 1955, LIEBIGS ANN CHEM, V591, P117 INAZU T, 1993, SYNLETT, V34, P4671 KLEINEWEISCHEDE R, 2008, ANGEW CHEM INT EDIT, V47, P5984, DOI 10.1002/anie.200801514 KOHN M, 2004, ANGEW CHEM INT EDIT, V43, P3106, DOI 10.1002/anie.200401744 KUROSAWA W, 2003, J AM CHEM SOC, V125, P8112, DOI 10.1021/ja036011k LIN FL, 2005, J AM CHEM SOC, V127, P2686, DOI 10.1021/ja044461m LLOYD K, 1968, CHEM COMMUN, P1400 MALKINSON JP, 2000, J ORG CHEM, V65, P5249 MASRIERA M, 1923, AN REAL SOC ESP QUIM, V21, P418 MOLINA P, 1991, TETRAHEDRON LETT, V32, P4041 MOLINA P, 1993, TETRAHEDRON, V49, P5153 MUKAIYAMA T, 1970, B CHEM SOC JPN, V43, P1271 MUKAIYAMA T, 1970, TETRAHEDRON LETT, P1901 NILSSON BL, 2000, ORG LETT, V2, P1939 NILSSON BL, 2005, ANNU REV BIOPH BIOM, V34, P91 PALACIOS F, 2007, TETRAHEDRON, V63, P523, DOI 10.1016/j.tet.2006.09.048 PARENTY A, 2006, CHEM REV, V106, P911 SANEYOSHI H, 2008, J ORG CHEM, V73, P9435, DOI 10.1021/jo8016132 SAXON E, 2000, SCIENCE, V287, P2007 SOELLNER MB, 2002, J ORG CHEM, V67, P4993 SOELLNER MB, 2006, J AM CHEM SOC, V128, P8820, ARTN JA060484K STAUDINGER H, 1919, HELV CHIM ACTA, V2, P635 STAUDINGER H, 1921, HELV CHIM ACTA, V4, P861 TIAN WQ, 2004, J ORG CHEM, V69, P4299, DOI 10.1021/jo049702n URPI F, 1986, TETRAHEDRON LETT, V27, P4623 URPI F, 1987, THESIS U BARCELONA VELASCO MD, 2000, TETRAHEDRON, V56, P4079 WAN Q, 2008, J AM CHEM SOC, V130, P15814, DOI 10.1021/ja804993y WIDAUER C, 1999, EUR J INORG CHEM OCT, P1659 ZALOOM J, 1985, J ORG CHEM, V50, P2601 ZBIRAL E, 1969, LIEBIGS ANN CHEM, P29 Bures, Jordi Martin, Manuel Urpi, Felix Vilarrasa, Jaume The Ministerio de Educacion y Ciencia [SAF2002-02728, CTQ-200615393]; Generalitat de Catalunya [2001SGR065] The Ministerio de Educacion y Ciencia contributed through Grant Nos. SAF2002-02728 and CTQ-200615393 and a studentship to J.B. and the Generalitat de Catalunya through Grant No. 2001SGR065. We acknowledge the work of authors who, over the last 15 years, have used the methods mentioned in the introduction, and we apologize for not citing them (cf. refs 4c-f). This study is dedicated to Prof. Teruaki Mukaiyama. Amer chemical soc Washington",
year = "2009",
doi = "10.1021/jo802825e",
language = "English",
volume = "74",
pages = "2203--2206",
journal = "The Journal of organic chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",

}

RIS

TY - JOUR

T1 - Catalytic Staudinger-Vilarrasa Reaction for the Direct Ligation of Carboxylic Acids and Azides

T2 - Journal of Organic Chemistry

AU - Bures, J.

AU - Martin, M.

AU - Urpi, F.

AU - Vilarrasa, J.

N1 - M1 - 5 ISI Document Delivery No.: 415GG Times Cited: 4 Cited Reference Count: 61 Cited References: AFONSO CAM, 1995, TETRAHEDRON LETT, V36, P8857 ALAJARIN M, 1999, J CHEM SOC PERK T 2, P1811 ARIZA X, 1998, TETRAHEDRON LETT, V39, P9101 ARIZA X, 1999, TETRAHEDRON LETT, V40, P7515 ARIZA X, 2001, TETRAHEDRON LETT, V42, P4995 BACHI MD, 1979, J ORG CHEM, V44, P4393 BARLUENGA J, 1990, J CHEM SOC P1, P2193 BASKIN JM, 2007, QSAR COMB SCI, V26, P1211, DOI 10.1002/qsar.200740086 BLANCOCANOSA JB, 2008, ANGEW CHEM INT EDIT, V47, P6851, DOI 10.1002/anie.200705471 BOSCH I, 1993, TETRAHEDRON LETT, V34, P4671 BOSCH I, 1995, J CHEM SOC CHEM 0107, P91 BOSCH I, 1996, J ORG CHEM, V61, P5638 CHAPUIS H, 2006, TETRAHEDRON, V62, P12108, DOI 10.1016/j.tet.2006.09.045 CHAPUIS H, 2008, TETRAHEDRON LETT, V49, P6838, DOI 10.1016/j.tetlet.2008.09.078 CHARAFEDDINE A, 2007, CHEM-EUR J, V13, P5566, DOI 10.1002/chem.200700058 CHARAFEDDINE A, 2007, ORG LETT, V9, P2787, DOI 10.1021/ol070818q COREY EJ, 1974, J AM CHEM SOC, V96, P5614 DAVID O, 2003, ANGEW CHEM INT EDIT, V42, P4373, DOI 10.1002/anie.200351930 DAWSON P, 2007, CHEM BIOL, V2, P567 EGUCHI S, 2005, ARKIVOC 2, P98 FRESNEDA PM, 2004, SYNLETT 0105, P1, DOI 10.1055/s-2003-43338 GARCIA J, 1984, TETRAHEDRON LETT, V25, P4841 GARCIA J, 1986, TETRAHEDRON LETT, V27, P639 GARCIA J, 1986, THESIS U BARCELONA GHOSH SK, 1992, TETRAHEDRON LETT, V33, P805 GHOSH SK, 1996, B CHEM SOC JPN, V69, P1705 HAASE C, 2008, ANGEW CHEM INT EDIT, V47, P6807, DOI 10.1002/anie.200801590 HACKENBERGER CPR, 2008, ANGEW CHEM INT EDIT, V47, P10030, DOI 10.1002/anie.200801313 HICKEY DMB, 1984, CHEM COMMUN, P776 HIEBL J, 1988, LIEBIGS ANN CHEM, P765 HORNER L, 1955, LIEBIGS ANN CHEM, V591, P117 INAZU T, 1993, SYNLETT, V34, P4671 KLEINEWEISCHEDE R, 2008, ANGEW CHEM INT EDIT, V47, P5984, DOI 10.1002/anie.200801514 KOHN M, 2004, ANGEW CHEM INT EDIT, V43, P3106, DOI 10.1002/anie.200401744 KUROSAWA W, 2003, J AM CHEM SOC, V125, P8112, DOI 10.1021/ja036011k LIN FL, 2005, J AM CHEM SOC, V127, P2686, DOI 10.1021/ja044461m LLOYD K, 1968, CHEM COMMUN, P1400 MALKINSON JP, 2000, J ORG CHEM, V65, P5249 MASRIERA M, 1923, AN REAL SOC ESP QUIM, V21, P418 MOLINA P, 1991, TETRAHEDRON LETT, V32, P4041 MOLINA P, 1993, TETRAHEDRON, V49, P5153 MUKAIYAMA T, 1970, B CHEM SOC JPN, V43, P1271 MUKAIYAMA T, 1970, TETRAHEDRON LETT, P1901 NILSSON BL, 2000, ORG LETT, V2, P1939 NILSSON BL, 2005, ANNU REV BIOPH BIOM, V34, P91 PALACIOS F, 2007, TETRAHEDRON, V63, P523, DOI 10.1016/j.tet.2006.09.048 PARENTY A, 2006, CHEM REV, V106, P911 SANEYOSHI H, 2008, J ORG CHEM, V73, P9435, DOI 10.1021/jo8016132 SAXON E, 2000, SCIENCE, V287, P2007 SOELLNER MB, 2002, J ORG CHEM, V67, P4993 SOELLNER MB, 2006, J AM CHEM SOC, V128, P8820, ARTN JA060484K STAUDINGER H, 1919, HELV CHIM ACTA, V2, P635 STAUDINGER H, 1921, HELV CHIM ACTA, V4, P861 TIAN WQ, 2004, J ORG CHEM, V69, P4299, DOI 10.1021/jo049702n URPI F, 1986, TETRAHEDRON LETT, V27, P4623 URPI F, 1987, THESIS U BARCELONA VELASCO MD, 2000, TETRAHEDRON, V56, P4079 WAN Q, 2008, J AM CHEM SOC, V130, P15814, DOI 10.1021/ja804993y WIDAUER C, 1999, EUR J INORG CHEM OCT, P1659 ZALOOM J, 1985, J ORG CHEM, V50, P2601 ZBIRAL E, 1969, LIEBIGS ANN CHEM, P29 Bures, Jordi Martin, Manuel Urpi, Felix Vilarrasa, Jaume The Ministerio de Educacion y Ciencia [SAF2002-02728, CTQ-200615393]; Generalitat de Catalunya [2001SGR065] The Ministerio de Educacion y Ciencia contributed through Grant Nos. SAF2002-02728 and CTQ-200615393 and a studentship to J.B. and the Generalitat de Catalunya through Grant No. 2001SGR065. We acknowledge the work of authors who, over the last 15 years, have used the methods mentioned in the introduction, and we apologize for not citing them (cf. refs 4c-f). This study is dedicated to Prof. Teruaki Mukaiyama. Amer chemical soc Washington

PY - 2009

Y1 - 2009

N2 - 2,2'-Dipyridyl diselenide (PySeSePy) is the catalyst or activator of choice for the direct reaction of carboxylic acids with azides and trimethylphosphine at room temperature. The mechanism of the process, which is not an aza-Wittig reaction, has been elucidated.

AB - 2,2'-Dipyridyl diselenide (PySeSePy) is the catalyst or activator of choice for the direct reaction of carboxylic acids with azides and trimethylphosphine at room temperature. The mechanism of the process, which is not an aza-Wittig reaction, has been elucidated.

KW - native chemical ligation oxidation-reduction condensation aza-wittig reaction one-pot preparation 2 redox reactions peptide synthesis synthetic tricks natural-products puromycin analogs glycosyl azides

U2 - 10.1021/jo802825e

DO - 10.1021/jo802825e

M3 - Article

VL - 74

SP - 2203

EP - 2206

JO - The Journal of organic chemistry

JF - The Journal of organic chemistry

SN - 0022-3263

ER -