Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2011(12): 1974-1983
DOI: 10.1055/s-0030-1260030
DOI: 10.1055/s-0030-1260030
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkKinetic Resolution of Secondary Alcohols by NHC-Catalyzed Oxidative Esterification
Further Information
Received
18 March 2011
Publication Date:
06 May 2011 (online)
Publication History
Publication Date:
06 May 2011 (online)
Abstract
Kinetic resolution of racemic secondary alcohols by oxidative esterification using carbene catalysis is described. Good to moderate selectivity has been achieved. N-Heterocyclic carbenes (NHCs) were systematically varied and several aldehydes were included in this study as acyl donors. As an oxidant, a readily available bisquinone-type system was used.
Key words
carbene catalysis - kinetic resolution - oxidative esterification - secondary alcohols - acylazolium ions
- 1a
Berkessel A.Gröger H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis Wiley-VCH; Weinheim: 2005. - 1b
Dalko PI. Enantioselective Organocatalysis: Reactions and Experimental Procedures Wiley-VCH; Weinheim: 2007. - For recent reviews on organocatalysis, see:
- 2a
Valero G.Companyo X.Bravo N.Alba A.-NR.Moyano A.Rios R. Synlett 2010, 1883 - 2b
Zhang ZG.Schreiner PR. Chem. Soc. Rev. 2009, 38: 1187 - 2c
Dondoni A.Massi A. Angew. Chem. Int. Ed. 2008, 47: 4638 - 2d
Pellissier H. Tetrahedron 2007, 63: 9267 - For recent reviews on NHC-catalyzed transformations, see:
- 3a
Nair V.Vellalath S.Babu BP. Chem. Soc. Rev. 2008, 37: 2691 - 3b
Enders D.Niemeier O.Henseler A. Chem. Rev. 2007, 107: 5606 - 3c
Marion N.Díez-González S.Nolan SP. Angew. Chem. Int. Ed. 2007, 46: 2988 - 3d
Zeitler K. Angew. Chem. Int. Ed. 2005, 44: 7506 - 4a
Lathrop SP.Rovis T. J. Am. Chem. Soc. 2009, 131: 13628 - 4b
Enders D.Henseler A. Adv. Synth. Catal. 2009, 351: 1749 - 5a
DiRocco DA.Oberg KM.Dalton DM.Rovis T. J. Am. Chem. Soc. 2009, 131: 10872 - 5b
Li Y.Shi F.-Q.He Q.-L.You S.-L. Org. Lett. 2009, 11: 3182 - 6a
Burstein C.Glorius F. Angew. Chem. Int. Ed. 2004, 43: 6205 - 6b
Sohn SS.Rosen EL.Bode JW. J. Am. Chem. Soc. 2004, 126: 14370 - For selected examples of NHC-catalyzed esterifications using internal redox reactions, see:
- 7a
Zeitler K.Rose CA. J. Org. Chem. 2009, 74: 1759 - 7b
Chow KY.-K.Bode JW. J. Am. Chem. Soc. 2004, 126: 8126 - 7c
Reynolds NT.Read de Alaniz J.Rovis T. J. Am. Chem. Soc. 2004, 126: 9518 - 7d
Grasa GA.Güveli T.Singh R.Nolan SP. J. Org. Chem. 2003, 68: 2812 - For NHC-catalyzed oxidative esterifications using an external oxidant, see:
- 8a
Maki BE.Chan A.Phillips EM.Scheidt KA. Tetrahedron 2009, 65: 3102 - 8b
Noonan C.Baragwanath L.Connon SJ. Tetrahedron Lett. 2008, 49: 4003 - 8c
Miyashita A.Suzuki Y.Nagasaki I.Ishiguro C.Iwamoto K.-I.Higashino T. Chem. Pharm. Bull. 1997, 45: 1254 - 8d
Tam SW.Jimenez L.Diederich F. J. Am. Chem. Soc. 1992, 114: 1503 - 9a
Campbell CD.Duguet N.Gallagher KA.Thomson JE.Lindsay AG.O’Donoghue AC.Smith AD. Chem. Commun. 2008, 3528 - 9b
Thomson JE.Rix K.Smith AD. Org. Lett. 2006, 8: 3785 - For selected examples of the nonenzymatic kinetic resolution of alcohols, see:
- 10a
Hu B.Meng M.Wang Z.Du W.Fossey JS.Hu X.Deng W.-P. J. Am. Chem. Soc. 2010, 132: 17041 - 10b
Rendler S.Plefka O.Karatas B.Auer G.Fröhlich R.Mück-Lichtenfeld C.Grimme S.Oestreich M. Chem. Eur. J. 2008, 14: 11512 - 10c
Vedejs E.Jure M. Angew. Chem. Int. Ed. 2005, 44: 3974 - 10d
Miller SJ. Acc. Chem. Res. 2004, 37: 601 - 11a
Suzuki Y.Yamauchi K.Muramatsu K.Sato M. Chem Commun. 2004, 2770 - 11b
Kano T.Sasaki K.Maruoka K. Org. Lett. 2005, 7: 1347 - For recent reports involving acylazolium ions, see:
- 12a
De Sarkar S.Studer A. Angew. Chem. Int. Ed. 2010, 49: 9266 ; Angew. Chem. 2010, 122, 9452 - 12b
Zhu ZQ.Xiao JC. Adv. Synth. Catal. 2010, 352: 2455 - 12c
Kaeobamrung J.Mahatthananchai J.Zheng P.Bode JW. J. Am. Chem. Soc. 2010, 132: 8810 - 12d
Ryan SJ.Candish L.Lupton DW. J. Am. Chem. Soc. 2009, 131: 14176 - For NHC-catalyzed transesterifications, see:
- 13a
Grasa GA.Güveli T.Singh R.Nolan SP. J. Org. Chem. 2003, 68: 2812 - 13b
Nyce GW.Lamboy JA.Connor EF.Waymouth RM.Hedrick JL. Org. Lett. 2002, 4: 3587 - 14a
De Sarkar S.Studer A. Org. Lett. 2010, 12: 1992 - 14b
De Sarkar S.Grimme S.Studer A. J. Am. Chem. Soc. 2010, 132: 1190 - 14c
Guin J.De Sarkar S.Grimme S.Studer A. Angew. Chem. Int. Ed. 2008, 47: 8727 ; Angew. Chem. 2008, 120, 8855 - 16 Bisquinone 14 is
readily prepared by treatment of 2,6-di-tert-butylphenol
(Aldrich US$37.50/1 kg) with O2; see:
Kharasch MS.Joshi BS. J. Org. Chem. 1957, 22: 1439 - 17
Enders D.Niemeier O.Balensiefer T. Angew. Chem. Int. Ed. 2006, 45: 1463 - 19
Brand JP.Siles JIO.Waser J. Synlett 2010, 881 - 20
Struble JR.Bode JW. Org. Synth. 2010, 87: 362 - 21
Vora HU.Lathrop SP.Reynolds NT.Kerr MS.deAlaniz JR.Rovis T. Org. Synth. 2010, 87: 350 - 22
Mahatthananchai J.Zheng P.Bode JW. Angew. Chem. Int. Ed. 2011, 50: 1673 - 23
Kagan HB.Fiaud JC. Top. Stereochem. 1988, 18: 249 - 24
Tietze LF.Kinzel T.Wolfram T. Chem. Eur. J. 2009, 15: 6199 - 25
Luo Y.Herndon JW.Cervantes-Lee F. J. Am. Chem. Soc. 2003, 125: 12720 - 26
Ryu E.-H.Cho HK.Zhao Y. Org. Lett. 2007, 9: 5147 - 27
Belletire JL.Bills RA.Shackelford SA. Synth. Commun. 2008, 38: 738 - 28
Enders D.Han J.Henseler A. Chem. Commun. 2008, 3989 - 29
Chênevert R.Pelchat N.Morin P. Tetrahedron: Asymmetry 2009, 20: 1191
References
Scheidt and co-workers reported the desymmetrization of meso-diols using oxidative carbene catalysis; see ref. 8a.
18The absolute configuration of the major enantiomer of 15a formed using catalyst 8 was determined by comparing the HPLC retention time with that of an authentic sample.