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Synthesis 2013; 45(7): 903-912
DOI: 10.1055/s-0032-1318136
DOI: 10.1055/s-0032-1318136
paper
Synthesis of Structure and Function Diverse α-D-Diazoacetates, α-D-Diazoacetamides, α-D-Diazoketones, and the Antibiotic α-D-Azaserine
Further Information
Publication History
Received: 28 October 2012
Accepted after revision: 08 January 2013
Publication Date:
04 March 2013 (online)
Abstract
Using 0.1 mol% to 1 mol% potassium carbonate in an acetonitrile–deuterium oxide mixture acts as a ‘privileged’ reaction system, which at ambient temperature affords, via a one-pot–one-cycle procedure, α-D-diazoacetates, α-D-diazoacetamides, or α-D-diazoketones from the corresponding nondeuterated form. The protocol is inexpensive, employs readily available materials, does not require harsh reaction conditions, requires two hours for completion, and affords the desired products in good yields and with excellent levels of deuterium incorporation. Exemplifying our protocol the first isotope labelled synthesis of N-Boc-α-D-azaserine with ≥95% D-incorporation is reported.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Thomas AF. Deuterium Labeling in Organic Chemistry . Appleton-Century-Crofts; New York: 1971
- 2a Mutlib AE. Chem. Res. Toxicol. 2008; 21: 1672
- 2b Birkemeyer C, Luedemann A, Wagner C, Erban A, Kopka J. Trends Biotechnol. 2005; 23: 28
- 2c Haskins NJ. Biomed. Mass Spectrom. 1982; 9: 269
- 3 Yan Z, Caldwell GW. Anal. Chem. 2004; 76: 6835
- 4 Tong CC, Hwang KC. J. Phys. Chem. C 2007; 111: 3490
- 6a Zhang Z, Wang J. Tetrahedron 2008; 64: 6577
- 6b Donaldson WA. Tetrahedron 2001; 57: 8589
- 6c Patai S. The Chemistry of Diazonium and Diazo Groups . Wiley; Chichester: 1978. Parts 1 and 2
- 6d Regitz M, Maas G. Diazo Compounds: Properties and Synthesis . Academic Press; Orlando: 1986
- 7 Sontakke CV, Patil SP, Unny VK. P, Sivaprasad N. J. Labelled Compd. Radiopharm. 2005; 48: 597
- 8 Johnson PL. J. Labelled Compd. Radiopharm. 2007; 50: 47
- 9 Ranocchiari M, Mezzetti A. Organometallics 2009; 28: 3611
- 10 Baldwin JE, Widdison WC. J. Am. Chem. Soc. 1992; 114: 2245
- 11a Baldwin JE, Patapoff TW, Barden TC. J. Am. Chem. Soc. 1984; 106: 1421
- 11b Baldwin JE, Carter CG. J. Am. Chem. Soc. 1978; 100: 3942
- 11c Baldwin JE, Carter CG. J. Am. Chem. Soc. 1982; 104: 1362
- 12 Keliher EJ, Burrell RC, Chobanian HR, Conkrite KL, Shukla R, Baldwin JE. Org. Biomol. Chem. 2006; 4: 2777
- 13 Ashwell S, Davies AG, Golding BT, Hay-Motherwell R, Mwesigye-Kibende S. J. Chem. Soc., Chem. Commun. 1989; 1483
- 14 Shafer J, Baronowsky P, Laursen R, Finn F, Westheimer FH. J. Biol. Chem. 1966; 241: 421
- 15 Cainelli G, Galletti P, Giacomini D, Licciulli S, Quintavalla A. Eur. J. Org. Chem. 2007; 2526
- 16 Qi X, Ready JM. Angew. Chem. Int. Ed. 2007; 46: 3242
- 17 Sen R, Widlanski TS, Balogh-Nair V, Nakanishi K. J. Am. Chem. Soc. 1983; 105: 5160
- 18 Mass G. Angew. Chem. Int. Ed. 2009; 48: 8186
- 19a deKeczer SA, Lane TS, Masjedizadeh MR. J. Labelled Compd. Radiopharm. 2004; 47: 733
- 19b Junk T, Catallo WJ. Tetrahedron Lett. 1996; 37: 3445
- 19c Werstiuk NH, Ju C. Can. J. Chem. 1989; 67: 812
- 19d Perrotin P, Sinnema P.-J, Shapiro PJ. Organometallics 2006; 25: 2104
- 20 Beak P, Monroe EM. J. Org. Chem. 1969; 34: 589
- 21 Roberts JD, Regan CM, Allen I. J. Am. Chem. Soc. 1952; 74: 3679
- 22 Baldwin J, Selden CB. J. Am. Chem. Soc. 1993; 115: 2239
- 23 Crombie L, Heavers AD. J. Chem. Soc., Perkin Trans. 1 1992; 1929
- 24 86th CRC Handbook of Chemistry and Physics . Linde DR. CRC Press; Boca Raton: 2008
- 25 We were concerned that MeOH may not be compatible with sensitive substrates such as 24. That acetone and a weak base may generate aldol byproducts and that DMSO and DMF may be difficult to efficiently remove from the sensitive α-D-diazo products
- 26 We used Romil UpS Ultra gradient MeCN (Code H050) that contained <0.0025% H2O. Throughout the study the ratio of MeCN–D2O was kept constant, i.e. 1.17:1 (v/v). Furthermore relative to the starting material, diazoacetate, the number of equivalents of MeCN and D2O was kept at 41:100 respectively unless otherwise indicated
- 27 Bew SP, Hiatt-Gipson GD, Lovell JA, Poullain C. Org. Lett. 2012; 14: 456
- 28 Toma T, Shimokawa J, Fukuyama T. Org. Lett. 2007; 9: 3195
- 29 Ouihia A, Rene L, Guilhem J, Pascard C, Badet B. J. Org. Chem. 1993; 58: 1641
- 30 Nawrat CC, Moody CJ. Nat. Prod. Rep. 2011; 28: 1426
- 31a Stock CC, Clarke DA, Reilly HC, Rhoads CP, Buckley SM. Nature (London, U. K.) 1954; 173: 71
- 31b Fusari SA, Frohardt RP, Ryder A, Haskell TH, Johannessen DW, Elder CC, Bartz QR. J. Am. Chem. Soc. 1954; 76: 2878
- 32 Ahluwalia GS, Grem JL, Hao Z, Cooney DA. Pharmacol. Ther. 1990; 46: 243
- 33 Wada K, Hiratake J, Irie M, Okada T, Yamada C, Kumagai H, Suzuki H, Fukuyama K. J. Mol. Biol. 2008; 380: 361
- 34 Zhang X, Ji J, Zhu Y, Jing C, Li M, Hu W. Org. Biomol. Chem. 2012; 10: 2133
- 35 Evans DA, Adams DJ, Kwan EE. J. Am. Chem. Soc. 2012; 134: 8162
- 36 Thornton ER, Keilbaugh SA. J. Am. Chem. Soc. 1983; 105: 3283
- 37 Tong Y.-Y, Dong Y.-Q, Du F.-S, Li Z.-C. Macromolecules 2008; 41: 7339
- 38 Balalai S, Mahdidoust M, Eshaghi-Najafabadi R. Chin. J. Chem. 2008; 26: 1141
- 39 Ouichi A, Rene L, Badet B. Tetrahedron Lett. 1992; 33: 5509
- 40 Shendage DM, Fröhlich R, Haufe G. Org. Lett. 2004; 6: 3675
- 41 Baumhof P, Mazitschek R, Giannis A. Angew. Chem. Int. Ed. 2001; 40: 3672