Highly Diastereoselective Ketone Aldol Reactions of Butane-2,3-diacetal Desymmetrised­ Glycolic Acid

Darren J.  Dixon; Antonio  Guarna; Steven V.  Ley; Alessandra  Polara; Félix  Rodríguez

doi:10.1055/s-2002-34377

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Highly Diastereoselective Ketone Aldol Reactions of Butane-2,3-diacetal Desymmetrised Glycolic Acid

Darren J. Dixon^a, Antonio Guarna^b, Steven V. Ley*^a, Alessandra Polara^a, Félix Rodríguez^a
^a Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK
Fax: +44(1223)336442; e-Mail: svl1000@cam.ac.uk;
^b Dipartimento di Chimica Organica ‘Ugo Schiff’, Università degli Studi di Firenze, Polo Scientifico, Via della Lastruccia, 13, 50019 Sesto Fiorentino, Italy

Abstract

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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

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References

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 Methods Scheffold 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

Highly Diastereoselective Ketone Aldol Reactions of Butane-2,3-diacetal Desymmetrised­ Glycolic Acid

Highly Diastereoselective Ketone Aldol Reactions of Butane-2,3-diacetal Desymmetrised Glycolic Acid