Diphenyl 2-pyridylphosphine and di-tert-butyl azodicarboxylate:convenient reagents for the Mitsunobu reaction

Tetrahedron Letters

Volumn 40, Issue 24, 1999, Pages 4497-4500

  Kiankarimi, Mehrak ^a   Lowe, Richard ^a   McCarthy, James R ^a   Whitten, Jeffrey P ^a  

^a NEUROCRINE BIOSCIENCES INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DICARBOXYLIC ACID DERIVATIVE; PHOSPHINE DERIVATIVE; REAGENT;

ARTICLE; DRUG ISOLATION; PURIFICATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033546351     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00819-9     Document Type: Article

References (10)

1. 1) The Mitsunobou reaction has been extensively reviewed, see: Mitsunobu, O. Synthesis 1981, 1. Simon, C; Sandor H.; Sandor, M., J. Heterocycl. Chem., 1997, 34, 349. Hughes, D. L. Org. Reactions, 1992, 42, 335.
2. 1) The Mitsunobou reaction has been extensively reviewed, see: Mitsunobu, O. Synthesis 1981, 1. Simon, C; Sandor H.; Sandor, M., J. Heterocycl. Chem., 1997, 34, 349. Hughes, D. L. Org. Reactions, 1992, 42, 335.
3. 1) The Mitsunobou reaction has been extensively reviewed, see: Mitsunobu, O. Synthesis 1981, 1. Simon, C; Sandor H.; Sandor, M., J. Heterocycl. Chem., 1997, 34, 349. Hughes, D. L. Org. Reactions, 1992, 42, 335.
4. 2) Two reports of the use of pyridyl diphenylphosphine and dimethylamino-triphenylphosphine in conjunction with diethyl azodicarboxylate have appeared. However these papers did not attempt to address the problems associated with the azodicarboxylate and its reduced form. Camp, D.; Jenkins, I. D. Aust. J. Chem. 1988, 41, 1835. Von Izstein, M.; Mocerino, M. Synth. Commun., 1990, 20, 2049.
5. 2) Two reports of the use of pyridyl diphenylphosphine and dimethylamino-triphenylphosphine in conjunction with diethyl azodicarboxylate have appeared. However these papers did not attempt to address the problems associated with the azodicarboxylate and its reduced form. Camp, D.; Jenkins, I. D. Aust. J. Chem. 1988, 41, 1835. Von Izstein, M.; Mocerino, M. Synth. Commun., 1990, 20, 2049.
6. 3) Available from Aldrich Chemical Co., Milwaukee, WI.
7. +).
8. 5) For a recent example of the application of Mitsunobu reaction to solid phase combinatorial chemistry see: Tunoori, A. R.; Dutta, D.; Georg, G. I. Tetrahedron Lett., 1998, 39, 8751.
9. 6) Examples of parallel solution phase synthesis using liquid extraction are: Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L. and Boger, D. L. J. Am. Chem. Soc. 1996, 118(11) 2567. Whitten, J. P.; Xie, Y. F.; Erickson, P. E.; Webb, T. R.; De Souza E. B.; Grigoriadis, D. E.; and McCarthy, J. R. J. Med. Chem. 1996, 39(22).
10. 6) Examples of parallel solution phase synthesis using liquid extraction are: Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L. and Boger, D. L. J. Am. Chem. Soc. 1996, 118(11) 2567. Whitten, J. P.; Xie, Y. F.; Erickson, P. E.; Webb, T. R.; De Souza E. B.; Grigoriadis, D. E.; and McCarthy, J. R. J. Med. Chem. 1996, 39(22).