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DOI: 10.1055/s-0028-1083503
Molecular Iodine in Protection and Deprotection Chemistry
Publikationsverlauf
Publikationsdatum:
01. Oktober 2008 (online)
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Abstract
The various reactions involving the protection and deprotection of functional groups effected by molecular iodine are described here.
1 Introduction
2 Iodine in Organic Synthesis
3 Molecular Iodine in Protection and Deprotection Chemistry
3.1 Protection Chemistry
3.1.1 Protection of Hydroxy Groups
3.1.2 Protection of Amines
3.1.3 Protection of Carbonyl Groups
3.2 Deprotection Chemistry
3.2.1 Deprotection of Carboxylic Esters
3.2.2 Hydrolysis of tert-Butyl Esters
3.2.3 Cleavage of p-Methoxybenzyl Ethers
3.2.4 Deprotection of Alkyl and Aryl Silyl Ethers
3.2.5 Cleavage of Allyl Ethers
3.2.6 Cleavage of Prenyl Ethers
3.2.7 Cleavage of Prenyl Carbamates
3.2.8 Selective Removal of Methoxy Protecting Groups in Carbohydrates
3.2.9 Selective Deprotection of Aromatic Acetates
3.2.10 Selective Deprotection of Acetylated Nucleosides
3.2.11 Depyranylation of Alcohols and Phenols
3.2.12 Chemoselective Deprotection of Acetals and Ketals
3.2.13 Chemoselective Hydrolysis of Terminal Acetonides
3.2.14 Deprotection of Thioacetals and Thioketals
3.2.15 Removal of the Amino-Protecting p-Methoxyphenyl Group
4 Conclusion
Key words
iodine - protection - deprotection - chemoselectivity - catalysis
-
1a
Lieben A. Justus Liebigs Ann. Chem. 1870, 7: 218 -
1b
Newman MS.Holmes HL. Org. Synth. Coll. Vol. II John Wiley & Sons; London: 1943. p.428 -
2a
House HO. Modern Synthetic Reactions W. A. Benjamin; Menlo Park CA: 1972. p.423, 428, 482 -
2b
Mundy BP.Ellerd MG. Name Reactions and Reagents in Organic Synthesis John Wiley & Sons; New York: 1988. p.372 -
2c
Clayden JP.Greeves N.Warren S.Wothers PD. Organic Chemistry Oxford University Press; London: 2002. 527. p.882 -
3a
Whitmore FC.Rothrock HS. J. Am. Chem. Soc. 1933, 55: 1106 -
3b
Rutherford KG.Mamer OA.Prokipcak JM.Jobin RA. Can. J. Chem. 1966, 44: 2377 -
3c
Jenner G. Tetrahedron Lett. 1988, 29: 2445 - 4
Baugault MJR. Acad. Sci. 1904, 139: 864 - 5
French AN.Bissmire S.Wirth T. Chem. Soc. Rev. 2004, 33: 354 -
6a
Zhang Z.Liu Q. Huaxue Jinzhan 2006, 18: 270 -
6b
Wang H.-S.Miao J.-Y.Zhao L.-F. Youji Huaxue 2005, 25: 615 - 7
Wang S.-Y. Synlett 2004, 2642 - 8
Banerjee AK.Vera W.Mora H.Laya MS.Bedoya L.Cabrera EV. J. Sci. Ind. Res. 2006, 65: 299 - 9
Togo H.Iida S. Synlett 2006, 2159 - 10
Green TW.Wuts PGM. Protecting Groups in Organic Synthesis 3rd ed.: John Wiley & Sons; New York: 1999. - 11
Karimi B.Golshani B. J. Org. Chem. 2000, 65: 7228 - 12
Saxena I.Deka N.Sarma JC.Tsuboi S. Synth. Commun. 2003, 33: 4005 - 13
Firouzabadi H.Iranpoor N.Sobhani S. Tetrahedron Lett. 2002, 43: 3653 - 14
Kumar HMS.Reddy BVS.Reddy EJ.Yadav JS. Chem. Lett. 1999, 857 - 15
Deka N.Sarma JC. Synth. Commun. 2000, 30: 4435 - 16
Deka N.Sarma JC. J. Org. Chem. 2001, 66: 1947 - 17
Ramalinga K.Vijayalakshmi P.Kaimal TNB. Tetrahedron Lett. 2002, 43: 879 - 18
Chavan SP.Kale RR.Shivasankar K.Chandake SI.Benjamin SB. Synthesis 2003, 2695 - 19
Borah R.Deka N.Sarma JC. J. Chem. Res., Synop. 1997, 110 - 20
Deka N.Mariotte A.-M.Boumendjel A. Green Chem. 2001, 3: 263 - 21
Phukan P. Tetrahedron Lett. 2004, 45: 4785 - 22
Kartha KPR.Field RA. Tetrahedron 1997, 53: 11753 - 23
Mukhopadhyay B.Kartha KPR.Russell DA.Field RA. J. Org. Chem. 2004, 69: 7758 - 24
Bosco JWJ.Agrahari A.Saikia AK. Tetrahedron Lett. 2006, 47: 4065 - 25
Ahmed N.van Lier JE. Tetrahedron Lett. 2006, 47: 5345 - 26
Kartha KPR. Tetrahedron Lett. 1986, 27: 3415 - 27
Deka N.Kalita DJ.Borah R.Sarma JC. J. Org. Chem. 1997, 62: 1563 - 28
Kalita DJ.Borah R.Sarma JC. Tetrahedron Lett. 1998, 39: 4573 - 29
Banik BK.Chapa M.Marquez J.Cardona M. Tetrahedron Lett. 2005, 46: 2341 - 30
Firouzabadi H.Iranpoor N.Hazarkhani H. J. Org. Chem. 2001, 66: 7527 - 31
Iranpoor N.Tamami B.Niknam K. Can. J. Chem. 1997, 75: 5 - 32
Samajdar S.Basu MK.Becker FF.Banik BK. Tetrahedron Lett. 2001, 42: 4425 - 33
Deka N.Sarma JC. Chem. Lett. 2001, 794 - 34
Shi B.Tang P.Hu X.Liu JO.Yu B. J. Org. Chem. 2005, 70: 10354 - 35
Zhang Y.Yu Y.Lin R. Org. Prep. Proced. Int. 1993, 365 - 36
Basu MK.Samajdar S.Becker FF.Banik BK. Synlett 2002, 319 - 37
Borah R.Kalita DJ.Sarma JC. Indian J. Chem.,
Sect. B 2002, 41: 1032 - 38
Karimi B.Golshani B. Synthesis 2002, 784 - 39
Rana KK.Guin C.Roy SC. J. Indian Chem. Soc. 2003, 60: 1005 - 40
Zahouily M.Mezdar A.Rakik J.Elmakssoudi A.Rayadh A.Sebti S. J. Mol. Catal. A: Chem. 2005, 233: 43 - 41
Cossy J.Albouy A.Scheloske M.Pardo DG. Tetrahedron Lett. 1994, 35: 1539 -
42a
Ghiya BJ.Soni PA.Doshi AG. Indian J. Chem., Sect. B 1986, 25: 759 -
42b
Wasim F.Jawaid F.Manchanda W.Shaidawara RW. J. Chem. Res., Synop. 1984, 9: 298 -
42c
Waghmare BY. M.Phil. Thesis University of Pune; India: 1998. -
42d
Gaikwad DD. M.Phil. Thesis University of Pune; India: 2003. - 43
Lokhande PD.Sakate SS.Taksande KN.Navghare B. Tetrahedron Lett. 2005, 46: 1573 - 44
Taksande KN.Sakate SS.Lokhande PD. Tetrahedron Lett. 2006, 47: 643 - 45
Yadav JS.Balanarsaiah E.Raghavendra S.Satyanarayana M. Tetrahedron Lett. 2006, 47: 4921 - 46
Vaino AR.Szarek WA. Synlett 1995, 1157 - 47
Vaino AR.Szarek WA. Chem. Commun. (Cambridge) 1996, 2351 - 48
Cotton FA.Wilkinson G. Advanced Inorganic Chemistry 5th ed.: Wiley; Toronto: 1988. - 49
Cruickshank FR.Benson SW. J. Phys. Chem. 1969, 73: 733 - 50
Lipshutz BH.Keith J. Tetrahedron Lett. 1998, 39: 2495 - 51
Thomas RM.Mohan GH.Iyengar DS. Tetrahedron Lett. 1997, 38: 4721 - 52
Yang SG.Park MY.Kim KH.Ruediger EH. Synlett 2002, 492 - 53
Vatèle J.-M. Synlett 2001, 1989 - 54
Vatèle J.-M. Tetrahedron 2002, 58: 5689 - 55
Vatèle J.-M. Tetrahedron Lett. 2003, 44: 9127 - 56
Boto A.Hernández D.Hernández R.Suárez E. Org. Lett. 2004, 6: 3785 - 57
Das B.Banerjee J.Ramu R.Pal R.Ravindranath N.Ramesh C. Tetrahedron Lett. 2003, 44: 5465 - 58
Ren B.Cai L.Zhang L.-R.Yang Z.-J.Zhang L.-H. Tetrahedron Lett. 2005, 46: 8083 - 59
Wahlstrom JL.Ronald RC. J. Org. Chem. 1998, 63: 6021 - 60
Sun J.Dong Y.Cao L.Wang X.Wang S.Hu Y. J. Org. Chem. 2004, 69: 8932 - 61
Szarek WA.Zamojski A.Tiwari KN.Ison ER. Tetrahedron Lett. 1986, 27: 3827 - 62
Yadav JS.Satyanarayana M.Raghavendra S.Balanarsaiah E. Tetrahedron Lett. 2005, 46: 8745 - 63
Nishide K.Yokota K.Nakamura D.Sumiya T.Node M.Ueda M.Fuji K. Tetrahedron Lett. 1993, 34: 3425 - 64
Verkade JMM.van Hemart LJC.Quaedflieg PJLM.Alsters PL.van Delft FL.Rutjes FPJT. Tetrahedron Lett. 2006, 47: 8109 - 65
Kalita DJ.Borah R.Sarma JC. J. Chem. Res., Synop. 1999, 404