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Synthesis 2002(14): 1973-1978
DOI: 10.1055/s-2002-34377
DOI: 10.1055/s-2002-34377
PAPER
© Georg Thieme Verlag Stuttgart · New York
Highly Diastereoselective Ketone Aldol Reactions of Butane-2,3-diacetal Desymmetrised Glycolic Acid
Further Information
Received
13 June 2002
Publication Date:
26 September 2002 (online)
Publication History
Publication Date:
26 September 2002 (online)
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Abstract
Butane-2,3-diacetal (BDA) desymmetrised glycolic acid building block 1 undergoes highly diastereoselective lithium enolate ketone aldol reactions with a range of methyl and mono-substituted methyl ketones to yield, after acid-catalysed deprotection, enantiopure α,β-dihydroxy acid derivatives bearing a quaternary carbon atom at the β-hydroxy centre.
Key words
diastereoselective reaction - ketone - aldol reaction - α-hydroxy acid - asymmetric synthesis
- 1
Murakami Y.Oshima Y.Yasumoto T. Nippon Suisan Gakkaishi 1982, 48: 69 ; Chem. Abstr. 1982, 96, 139380 - 2
West LM.Northcote PT.Battershill CN. J. Org. Chem. 2000, 65: 445 - 3
Coppola GM.Schuster HF. α-Hydroxy Acids in Enantioselective Synthesis VCH; Weinheim: 1997. - 4
Hanessian S. Total Synthesis of Natural Products: The Chiron Approach Pergamon; Oxford: 1983. -
5a
Davis FA.Chen B.-C. Chem. Rev. 1992, 92: 919 -
5b
Evans DA.Morrissey MM.Dorow RL. J. Am. Chem. Soc. 1985, 107: 4346 -
6a
Pansare SV.Ravi RG.Jain RP. J. Org. Chem. 1998, 63: 4120 -
6b
Pansare SV.Ravi RG. Tetrahedron 1998, 54: 14549 -
7a
Byun IS.Kim YH. Synth. Commun. 1995, 25: 1963 -
7b
Burk MJ.Kalberg CS.Pizzano A. J. Am. Chem. Soc. 1998, 120: 4345 -
7c
Brown HC.Cho BT.Park WS. J. Org. Chem. 1986, 51: 3396 -
7d
Wang Z.La B.Fortunak JM.Meng XJ.Kabalka GW. Tetrahedron Lett. 1998, 39: 5501 - 8
Ooi T.Miura T.Takaya K.Ichikawa H.Maruoka K. Tetrahedron 2001, 57: 867 ; and references cited therein - For examples, see:
-
9a
Belokon YN.Green B.Ikonnikov NS.North M.Parsons T.Tararov VI. Tetrahedron 2001, 57: 771 -
9b
Hanefeld U.Li YX.Sheldon RA.Maschmeyer T. Synlett 2000, 1775 ; and references cited therein - 10
Huerta FF.Laxmi YRS.Buckvall J.-E. Org. Lett. 2000, 2: 1037 -
11a
Kim M.-J.Whitesides GM. J. Am. Chem. Soc. 1988, 110: 2959 -
11b
Adam W.Lazarus M.Boss B.Saha-Moller CR.Humpf H.-U.Schreier P. J. Org. Chem. 1997, 62: 7841 -
12a
Yu H.Ballard CE.Wang B. Tetrahedron Lett. 2001, 42: 1835 -
12b
Andrus MB.Soma Sekhar BBV.Meredith EL.Kent Dalley N. Org. Lett. 2000, 2: 3035 -
12c
Crimmins MT.Emmitte KA.Katz JD. Org. Lett. 2000, 2: 2165 -
12d
Chang J.-W.Jang D.-P.Uang B.-J.Liao F.-L.Wang S.-L. Org. Lett. 1999, 1: 2061 -
12e
Pearson WH.Cheng M.-C. J. Org. Chem. 1987, 52: 3176 -
12f
Seebach D.Naef R. Helv. Chim. Acta 1981, 64: 2704 -
12g
Seebach D. In Modern Synthetic MethodsScheffold R. Springer; Heidelberg: 1986. p.125-257 -
13a
Bezuidenhoudt BCB.Castle GH.Ley SV. Tetrahedron Lett. 1994, 35: 7447 -
13b
Bezuidenhoudt BCB.Castle GH.Geden JV.Ley SV. Tetrahedron Lett. 1994, 35: 7451 -
13c
Castle GH.Ley SV. Tetrahedron Lett. 1994, 35: 7455 -
13d
Boons G.-J.Downham R.Kim KS.Ley SV.Woods M. Tetrahedron 1994, 50: 7157 -
13e
Downham R.Kim KS.Ley SV.Woods M. Tetrahedron Lett. 1994, 35: 769 - 14
Morita H.Kishi E.Takeya K.Itokawa H.Iitaka Y. Phytochem. 1993, 33: 691 - 15
Hansawasdi C.Kawabata J.Kasai T. Biosci. Biotechnol. Biochem. 2000, 64: 1041 - 16
Ley SV.Baeschlin DK.Dixon DJ.Foster AC.Ince SJ.Priepke HWM.Reynolds DJ. Chem. Rev. 2001, 101: 53 - 17
Diez E.Dixon DJ.Ley SV. Angew. Chem. Int. Ed. 2001, 40: 2906 - 18
Dixon DJ.Ley SV.Rodríguez F. Org. Lett. 2001, 3: 3753 - 19
Dixon DJ.Ley SV.Rodríguez F. Angew. Chem. Int. Ed. 2001, 40: 4763 - 20
Dixon DJ.Ley SV.Polara A.Sheppard T. Org. Lett. 2001, 3: 3749 - 21 Calculated from Macromodel’s
version of the MM2 forcefield, see:
Mohamadi F.Richards NGJ.Guida WC.Liskamp R.Lipton M.Caufield C.Chang G.Hendrickson T.Still WC. J. Comp. Chem. 1990, 11: 440