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Synthesis 2006(17): 2841-2844
DOI: 10.1055/s-2006-942516
DOI: 10.1055/s-2006-942516
PAPER
© Georg Thieme Verlag Stuttgart · New York
One-Step Tethering of ω-Mercaptoalkyl Function to Alcohols
Further Information
Received
21 March 2006
Publication Date:
25 July 2006 (online)
Publication History
Publication Date:
25 July 2006 (online)
Abstract
A new method of attachment of ω-mercaptoalkyl function to primary, secondary, and tertiary hydroxy groups based on ω-mercaptoalkyl monomalonates is reported. The attachment process proceeds in one stage and does not require a deprotection step thus directly providing high yields of unsymmetric malonates possessing a terminal thiol functionality.
Key words
thiols - acylations - chemoselectivity - esters - self-assembly
- See reviews:
-
1a
Ulman A. Chem. Rev. 1996, 96: 1533 -
1b
Witt D.Klajn R.Barski P.Grzybowski BA. Curr. Org. Chem. 2004, 8: 1763 -
2a
Kumar A.Biebuyck HA.Abbott NL.Whitesides GM. J. Am. Chem. Soc. 1992, 114: 9188 -
2b
Piner RD.Zhu J.Xu F.Hong S.Mirkin CA. Science 1999, 283: 661 - 3
Gittins DI.Bethell D.Schiffrin DJ.Nichols RJ. Nature (London) 2000, 408: 67 - 4 See review:
Katz E.Willner I. Angew. Chem. Int. Ed. 2004, 43: 6042 - 5
McRipley MA.Linsenmeier RA. J. Electroanal. Chem. 1996, 414: 235 - 6
Jennings GK.Laibinis PE. J. Am. Chem. Soc. 1997, 119: 5208 - 7
McDermott MT.Green JBD.Porter MD. Langmuir 1997, 13: 2504 - 8
Aizenberg J.Black AJ.Whitesides GM. Nature (London) 1999, 398: 495 -
9a
Delfino JM.Schreiber SL.Richards FM. J. Am. Chem. Soc. 1993, 115: 3458 -
9b
Delfino JM.Stankociv CJ.Schreiber SL.Richards FM. Tetrahedron Lett. 1987, 28: 2323 -
9c
Livni E.Davis MA.Warner VD. J. Med. Chem. 1979, 22: 580 -
10a
Camarero JA.Kwon Y.Coleman MA. J. Am. Chem. Soc. 2004, 126: 14730 -
10b
Patel N.Davies MC.Harshorne M.Heaton RJ.Roberts CJ.Tendler SJB.Williams PM. Langmuir 1997, 13: 6485 -
10c
Ball JC.Puckett LG.Bachas LG. Anal. Chem. 2003, 75: 6932 -
11a
Pole-Grosdemange C.Simon ES.Prime KL.Whitesides GM. J. Am. Chem. Soc. 1991, 113: 12 -
11b
Roberts C.Chen CS.Mrksich M.Martichomok V.Donald DE.Whitesides GM. J. Am. Chem. Soc. 1998, 120: 6548 -
12a
Horton RC.Herne TM.Myles DC. J. Am. Chem. Soc. 1997, 119: 12980 -
12b
Sigal GB.Bamdad C.Barberis A.Strominger J.Whitesides GM. Anal. Chem. 1996, 68: 490 -
13a
Kitov IP.Railton C.Bundle DR. Carbohydr. Res. 1998, 307: 361 -
13b
Aherne D.Rao SN.Fitzmaurice D. J. Phys. Chem. B 1999, 103: 1821 -
13c
Ayers JT.Anderson SR. Synth. Commun. 1999, 29: 351 -
14a
Ye S.Yashiro A.Sato Y.Uosaki K. J. Chem. Soc., Faraday Trans. 1996, 3813 -
14b
Kwon Y.Mrksich M. J. Am. Chem. Soc. 2002, 124: 806 -
14c
Yousaf MN.Houseman BT.Mrksich M. Angew. Chem. Int. Ed. 2001, 40: 1093 - 15
Bednarski PJ.Nelson SD. J. Med. Chem. 1989, 32: 203 -
16a
Callahan FM.Anderson GW.Paul R.Zimmerman JE. J. Am. Chem. Soc. 1963, 85: 201 -
16b
Pastuszak JJ.Chimiak A. J. Org. Chem. 1981, 46: 1868 - 17
Zervas L.Theodoropoulos DM. J. Am. Chem. Soc. 1956, 78: 1359 - 18
Green TW.Wuts PGM. Protective Groups in Organic Synthesis John Wiley & Sons; New York: 1999. p.454-493 - 19
Shelkov R.Nahmany M.Melman A. Org. Biomol. Chem. 2004, 2: 397 - 20
Shelkov R.Nahmany M.Melman A. J. Org. Chem. 2002, 67: 8975 -
21a
Chiang Y.Guo H.-X.Kresge AJ.Tee OS. J. Am. Chem. Soc. 1996, 118: 3386 -
21b
Chiang Y.Kresge AJ.Meng Q.Morita Y.Yamamoto Y. J. Am. Chem. Soc. 1999, 121: 8345 - 22
Mourtas S.Katakalou C.Nicolettou A.Tzavara C.Gatos D.Barlos K. Tetrahedron Lett. 2003, 44: 179 - 23
Bodanszky M.Bodanszky A. Int. J. Pept. Protein Res. 1984, 23: 565