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Synlett 2011(5): 712-716
DOI: 10.1055/s-0030-1259550
DOI: 10.1055/s-0030-1259550
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New YorkThe First Organocatalysed Direct Aldol Reaction of 2-Hydroxycyclobutanone
Further Information
Received
16 December 2010
Publication Date:
11 February 2011 (online)
Publication History
Publication Date:
11 February 2011 (online)
Abstract
l-Tryptophan has been shown to catalyse the enantioselective aldol reaction between 2-hydroxycyclobutanone and an aromatic aldehyde in DMF solution. The reaction is completely regioselective and gives the 2,2-disubstituted cyclobutanone in up to 80% yield. The major adduct is obtained with ee values up to 67%, and has an anti relative configuration which contrasts with the selectivity of organocatalysed aldol reactions conducted on acyclic hydroxyacetone substrates.
Key words
cyclobutanone - tryptophan - organocatalysis - aldol reaction - stereoselective reaction.
- 1a
Namsylo JC.Kaufmann DE. Chem. Rev. 2003, 103: 1485 - 1b
Lee-Ruff E.Mladenova G. Chem. Rev. 2003, 103: 1449 - 1c
Fu N.-Y.Chan S.-H. In The Chemistry of CyclobutanesRappoport Z.Liebman JF. Wiley and Sons; Chichester: 2005. p.357 - 1d
Lee-Ruff E. In The Chemistry of CyclobutanesRappoport Z.Liebman JF. Wiley and Sons; Chichester: 2005. p.281 - 2a
Bellus D.Ernst B. Angew. Chem., Int. Ed. Engl. 1988, 27: 797 - 2b
Nemoto H.Fukumoto K. Synlett 1997, 863 - 2c
Salaün J. Science of Synthesis Vol. 26:Cossy J. Thieme; Stuttgart: 2004. p.557 - 3a
Miyata J.Nemoto H.Ihara M. J. Org. Chem. 2000, 65: 504 - 3b
Kingsbury JS.Corey EJ. J. Am. Chem. Soc. 2005, 127: 13813 - 3c
Wang B.Shen Y.-M.Shi Y.
J. Org. Chem. 2006, 71: 9519 - 3d
Hiroi K.Nakamura H.Anzai T. J. Am. Chem. Soc. 1987, 109: 1250 - 3e
Nemoto H.Nagamochi M.Fukumoto K. J. Org. Chem. 1992, 57: 1707 - 3f
Nemoto H.Nagamochi M.Ishibashi H.Fukumoto K. J. Org. Chem. 1994, 59: 74 - For some recent reviews on organocatalysis, see:
- 4a
Melchiorre P.Marigo M.Carlone A.Bartoli G. Angew. Chem. Int. Ed. 2008, 47: 6138 - 4b
Dondoni A.Massi A. Angew. Chem. Int. Ed. 2008, 47: 2 - 4c
Erkkila A.Majander I.Pihko PM. Chem. Rev. 2007, 107: 5416 - 4d
Mukherjee S.Yang JW.Hoffmann S.List B. Chem. Rev. 2007, 107: 5471 - 4e
Pellissier H. Tetrahedron 2007, 63: 9267 - 4f
Guillena G.Najera C.Ramon DJ. Tetrahedron: Asymmetry 2007, 18: 2249 - 4g
Dalko PI. Enantioselective Organocatalysis Wiley-VCH; Weinheim: 2007. - 4h
Berkessel A.Gröger H. Asymmetric Organocatalysis Wiley-VCH; Weinheim: 2005. - 5
Zhang L.Cui L.Li X.Li J.Luo S.Cheng J.-P. Chem. Eur. J. 2010, 16: 2045 - 6
Kotrusz P.Alemayehu S.Toma S.Schmalz H.-G.Adler A. Eur. J. Org. Chem. 2005, 4904 - 7a
Kotrusz P.Kmentová I.Gotov B.Toma S.Solčánioná E. Chem. Commun. 2002, 2510 - 7b
Cobb AJ.Shaw DM.Longbottom DA.Gold JB.Ley SV. Org. Biomol. Chem. 2005, 3: 84 - 7c
Alcaide B.Almendros P.Luna A. Tetrahedron 2007, 63: 3102 - 7d
Ma X.Da C S.Yi L.Jia Y.-N.Guo Q.-P.Che L.-P.Wu F.-C.Wang J.-R.Li W.-P. Tetrahedron: Asymmetry 2009, 20: 1419 - 8a
Cobb AJA.Shaw DM.Ley SV. Synlett 2004, 558 - 8b
Alza E.Rodríguez-Escrich C.Sayalero S.Bastero A.Pericàs MA. Chem. Eur. J. 2009, 15: 10167 - 8c
Veverková E.Štrasserová J.Šebesta R.Toma Š. Tetrahedron: Asymmetry 2010, 21: 58 - 9
Kotrusz P.Toma S.Schmalz H.-G.Adler A. Eur. J. Org. Chem. 2004, 1577 - 10a
Alberti G.Bernard AM.Floris C.Frongia A.Piras PP.Secci F.Spiga M. Org. Biomol. Chem. 2009, 7: 3512 - 10b
Frongia A.Girard C.Ollivier J.Piras PP.Secci F. Synlett 2008, 2823 - 10c
Bernard AM.Frongia A.Guillot R.Piras PP.Secci F.Spiga M. Org. Lett. 2007, 9: 541 - 10d
Secci F.Frongia A.Ollivier J.Piras PP. Synthesis 2007, 999 - 10e
Bernard AM.Frongia A.Piras PP.Secci F. Org. Lett. 2003, 5: 2923 - 10f
Chevtchouk T.Ollivier J.Salaün J. Tetrahedron: Asymmetry 1997, 8: 1011 - 10g
Bernard AM.Frongia A.Piras PP.Secci F. Chem. Commun. 2005, 3853 - 11a
Le Liepvre M.Ollivier J.Aitken DJ. Tetrahedron: Asymmetry 2010, 21: 1480 - 11b
Le Liepvre M.Ollivier J.Aitken DJ. Eur. J. Org. Chem. 2009, 5953 - 11c
Fernandes C.Pereira E.Faure S.Aitken DJ. J. Org. Chem. 2009, 74: 3217 - 11d
Mondière A.Peng R.Remuson R.Aitken DJ. Tetrahedron 2008, 64: 1088 - 11e
Fernandes C.Gauzy C.Yang Y.Roy O.Pereira E.Faure S.Aitken DJ. Synthesis 2007, 2222 - 11f
Gauzy C.Saby B.Pereira E.Faure S.Aitken DJ. Synlett 2006, 1394 - 11g
Gu X.Xian M.Roy-Faure S.Bolte J.Aitken DJ.Gefflaut T. Tetrahedron Lett. 2006, 47: 193 - 11h
Gauzy C.Pereira E.Faure S.Aitken DJ. Tetrahedron Lett. 2004, 45: 7095 - 11i
Aitken DJ.Gauzy C.Pereira E. Tetrahedron Lett. 2004, 45: 2359 - 11j
Aitken DJ.Gauzy C.Pereira E. Tetrahedron Lett. 2002, 43: 6177 - 11k
Vergne F.Partogyan K.Aitken DJ.Husson H.-P. Tetrahedron 1996, 52: 2421 - 12a
Bella M.Gasperi T. Synthesis 2009, 1583 - 12b
Quaternary
Stereocenters: Challenge and Solutions for Organic Synthesis
Christoffers J.Baro A. Wiley-VCH; Weinheim: 2005. - Recent examples of the preparation and synthetic transformations of 2-hydroxymethyl-2-hydroxycyclobutanone derivatives:
- 13a
Maulide N.Markó IE. Org. Lett. 2007, 9: 3757 - 13b
Gao F.Burnell DJ.
J. Org. Chem. 2006, 71: 356 - 13c
Zhang X.Li WZ. Synth. Commun. 2006, 36: 249 - 13d
Li WZ.Zhang X. Org. Lett. 2002, 4: 3485 - 13e
Kawafuchi H.Inokuchi T. Tetrahedron Lett. 2002, 43: 2051 - 13f
Blanchard AN.Burnell DJ. Tetrahedron Lett. 2001, 42: 4779 - 13g
Hanna I.Ricard L. Tetrahedron Lett. 1999, 40: 863 - 13h
Kanada RM.Taniguchi T.Ogasawara K. Chem. Commun. 1998, 1755 - 13i
Crane SN.Burnell DJ. J. Org. Chem. 1998, 63: 5708 - 13j
Crane SN.Jenkins TJ.Burnell DJ. J. Org. Chem. 1997, 62: 8722 - 13k
Lin X.Kavash RW.Mariano PS.
J. Org. Chem. 1996, 61: 7335 - 14
Kotsuki H.Ikishima H.Okuyama A. Heterocycles 2008, 75: 493 ; and references therein - 15
Xu L.-W.Lu Y. Org. Biomol. Chem. 2008, 6: 2047 - 16a
Jiang Z.Yang H.Han X.Luo J.Wong MW.Lu Y. Org. Biomol. Chem. 2010, 8: 1368 - 16b
Hayashi Y.Itoh T.Nagae N.Ohkubo M.Ishikawa H. Synthesis 2008, 1565 - 16c
Ramasastry SSV.Zhang H.Tanaka F.Barbas CF. J. Am. Chem. Soc. 2007, 129: 288 - 16d
Ramasastry SSV.Albertshofer K.Utsumi N.Tanaka F.Barbas CF. Angew. Chem. Int. Ed. 2007, 46: 5572 - 16e
Utsumi N.Imai M.Tanaka F.Ramasastry SSV.Barbas CF. Org. Lett. 2007, 9: 3445 - 16f
Wu X.Jiang Z.Shen H.-M.Lu Y. Adv. Synth. Catal. 2007, 812 - 16g
Teo Y.-C. Tetrahedron: Asymmetry 2007, 18: 1155 - 16h
Córdova A.Zou W.Dziedzic I.Ibrahem I.Reyes E.Xu Y. Chem. Eur. J. 2006, 12: 5383 - 16i
Amedijkouh M. Tetrahedron: Asymmetry 2005, 16: 1411 - 19
Xu X.-Y.Wang Y.-Z.Gong L.-Z. Org. Lett. 2007, 9: 4247
References
Very recently it was reported that l-Trp did not catalyse the aldol reaction of hydroxyacetone with 4 in water, see ref. 16a.
18CCDC 772896 contains the supplementary crystallographic data for anti-4. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.