RSS-Feed abonnieren
DOI: 10.1055/s-2008-1067226
A Synthesis of 1-Lithiated Glycals and 1-Tributylstannyl Glycals from 1-Phenylsulfinyl Glycals via Sulfoxide-Lithium Ligand Exchange
Publikationsverlauf
Publikationsdatum:
13. August 2008 (online)
Abstract
1-Lithiated glycals generated by reaction of 1-phenylsulfinyl glycals with either t-BuLi or PhLi are transformed to 1-tributylstannyl glycals on reaction with tributyltin chloride.
Keywords
lithium - tin - sulfoxides - carbohydrates - glycals
- Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0001th:
- Primary Data (added August 26th, 2009). FIDs and associated files for the 1H, 13C and DEPT NMR spectra for compounds 14, (S S)-23, (S S)-25, (R S)-26, 27, (S S)-28, (R S,S S)-29, 30, (R S)-36, (S S)-36, (S S)-37, 38, (R S)-39, (S S)-39, (S S)-44, (R S)-46, (S S)-46, (R S)-48, (S S)-48, (S S)-49, 52, (R S)-53, (R S)-55, (R S)-57, (S S)-57, (S S)-58, (R S)-61, (S S)-61, (R S)-62, (S S)-62, (R S)-65 and (S S)-65 are summarized.
-
1a
Jarosz S.Zamojski A. Curr. Org. Chem. 2003, 7: 13 -
1b
Somsák L. Chem. Rev. 2001, 101: 81 -
2a
Friesen RW.Loo RW. J. Org. Chem. 1991, 56: 4821 -
2b
Dubois E.Beau J.-M. Carbohydr. Res. 1992, 223: 157 - 3
Dubois E.Beau J.-M. Carbohydr. Res. 1992, 228: 103 - 4
Tius MA.Gomez-Galeno J.Gu X.-qZ.Javid H. J. Am. Chem. Soc. 1991, 113: 5775 - 5
Zhang H.-C.Brakta M.Doyle Daves G. Tetrahedron Lett. 1993, 34: 1571 - 6
Koo B.McDonald FE. Org. Lett. 2005, 7: 3621 - 7
Steunenberg P.Jeanneret V.Zhu Y.-H.Vogel P. Tetrahedron Asymmetry 2005, 16: 337 - 8
Dubbaka SR.Steunenberg P.Vogel P. Synlett 2004, 1235 - 9
Lesimple P.Beau J.-M.Sinaÿ P. J. Chem. Soc., Chem. Commun. 1985, 894 - 10
Hanessian S.Martin M.Desai RC. J. Chem. Soc., Chem. Commun. 1986, 926 - 11
Bearder JR.Dewis ML.Whiting DA. J. Chem. Soc., Perkin Trans.1 1995, 227 - 12
Parker KA.Su D.-S. J. Carbohydr. Chem. 2005, 24: 187 -
13a
Parker KA.Coburn CA.Koh Y. J. Org. Chem. 1995, 60: 2938 -
13b
Koyama Y.Yamaguchi R.Suzuki K. Angew. Chem. Int. Ed. 2008, 47: 1084 - 14
Dötz KH.Otto F.Nieger M. J. Organomet. Chem. 2001, 621: 77 - 15
Hallett MR.Painter JE.Quayle P.Ricketts D. Tetrahedron Lett. 1998, 39: 2851 - 16
Milne JE.Jarowicki K.Kocienski PJ.Alonso J. Chem. Commun. 2002, 426 - 17 Review:
Friesen RW. J. Chem. Soc., Perkin Trans. 1 2001, 1969 - 18
Boeckman RK.Bruza KJ. Tetrahedron 1981, 37: 3997 - 19 Glycals with heteroatom substituents
(Cl, OR, SR) at C2 rapidly metallate with n-BuLi,
conditions that are compatible with benzyl ether protecting groups:
Boyd E.Hallet MR.Jones RVH.Painter JE.Patel P.Quayle P.Waring AJ. Tetrahedron Lett. 2006, 47: 8337 ; and references cited therein - 20
Friesen RW.Sturino CF.Daljeet AK.Kolaczewska A. J. Org. Chem. 1991, 56: 1944 -
21a
Friesen RW.Trimble LA. J. Org. Chem. 1996, 61: 1165 -
21b
Imanieh H.Quayle P.Voaden M.Street SDA. Tetrahedron Lett. 1992, 33: 543 -
21c
Crich D.Ritchie TJ. Tetrahedron 1988, 44: 2319 - 22
Jäkel C.Dötz KH. J. Organomet. Chem. 2001, 624: 172 - 23
Paquette LA.Oplinger JA. Tetrahedron 1989, 45: 107 - 24
Majumder U.Cox JM.Johnson HWB.Rainier JD. Eur. J. Org. Chem. 2006, 12: 1736 -
25a
Friesen RW.Loo RW.Sturino CF. Can. J. Chem. 1994, 72: 1262 -
25b
Jäkel C.Dötz KH. Tetrahedron 2000, 56: 2167 - 26
Parker KA.Su D.-S. J. Org. Chem. 1996, 61: 2191 - 27
Lesimple P.Beau J.-M.Jaurand G.Sinaÿ P. Tetrahedron Lett. 1986, 27: 6201 - 28
Gunn A.Jarowicki K.Kocienski P.Lockhart S. Synthesis 2001, 331 - 31
Furukawa N.Sato S. In Topics in Current Chemistry Vol. 205:Page PCB. Springer; Berlin: 1999. p.89-129 - 32
Theobald P.Okamura WH. J. Org. Chem. 1990, 55: 741 -
33a
Lockard JP.Schroeck CW.Johnson CR. Synthesis 1973, 485 -
33b
Durst T.LeBelle MJ.Elzen R.Tin KC. Can. J. Chem. 1974, 52: 761 -
33c
Clayden J.Mitjans D.Youssef LH. J. Am. Chem. Soc. 2002, 124: 5266 - 34
Sakurada J.Satoh T. Tetrahedron 2007, 63: 3806 - 35
Blakemore PR.Burge MS. J. Am. Chem. Soc. 2007, 129: 3068 - 36
Hoffmann RW. Chem. Soc. Rev. 2003, 32: 225 - 37
Satoh T. Chem. Rev. 1996, 96: 3303 - 38
Carpintero M.Nieto I.Fernández-Mayoralas A. J. Org. Chem. 2001, 66: 1768 - 39
Lipton MF.Sorenson CM.Sadler AC.Shapiro RH. J. Organomet. Chem. 1980, 186: 155 - 41
Fernández-Mayoralas A.Marra A.Trumtel M.Veyrieres A.Sinaÿ P. Carbohydr. Res. 1989, 188: 81 - 42
Chen X.-T.Bhattacharya SK.Zhou B.Gutteridge CE.Pettus TRR.Danishefsky SJ. J. Am. Chem. Soc. 1999, 121: 6563 - 43
Yu W.Jin Z. J. Am. Chem. Soc. 2002, 124: 6576 - 44
Nicolaou KC.Trujillo JI.Chibale K. Tetrahedron 1997, 53: 8751 - 45
Jin YH.Liu P.Wang J.Baker R.Huggins J.Chu CK. J. Org. Chem. 2003, 68: 9012 - 46
Fürstner A. Liebigs Ann. Chem. 1993, 1211 - 47
Kast J.Hoch M.Schmidt RR. Liebigs Ann. Chem. 1991, 481 - 48
Damager I.Olsen CE.Moller BL.Motawia MS. Carbohyr. Res. 1999, 320: 19
References
The Bu3SnMgBr was prepared by transmetallation of Bu3SnLi with MgBr2. The Bu3SnLi was prepared, in turn, by the reaction of BuLi with Bu3SnSnBu3 thereby generating 1 equiv of Bu4Sn waste for each equiv of Bu3SnLi.
30Parker and Su (reference 26) reported a successful metallation of the bis-TBS-protected analogue of 35 using 3 equiv of t-BuLi in THF at -78 ˚C.
40Crystallographic data for the structures in this paper have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 685328 [( S S )-44], 676297 [(R S)-36], 676296 [(R S)-48], 676300 [(R S)-55], 676298 [(S S)-28], 676301 [(S S)-61], 682926 [(S S)-37]. Copies of these data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk or via www.ccdc.cam.ac.uk/conts/retrieving.html.