Regio- and Stereoselective Approach to 1,4-Ditertiary Carbinols from Dimethyl Tartrate

Tuvshinjargal Budragchaa; Alexander Roller; Michael Widhalm

doi:10.1055/s-0032-1317168

Synthesis, Table of Contents

Synthesis 2012; 44(20): 3238-3250
DOI: 10.1055/s-0032-1317168

paper

Regio- and Stereoselective Approach to 1,4-Ditertiary Carbinols from Dimethyl Tartrate

Authors

Tuvshinjargal Budragchaa

^aInstitute of Organic Chemistry, Faculty of Chemistry, University of Vienna, Währinger Straße 38, 1090 Wien, Austria, Fax: +43(1)42779521 Email: m.widhalm@univie.ac.at
Alexander Roller

^bInstitute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Währinger Straße 42, 1090 Wien, Austria
Michael Widhalm*

^aInstitute of Organic Chemistry, Faculty of Chemistry, University of Vienna, Währinger Straße 38, 1090 Wien, Austria, Fax: +43(1)42779521 Email: m.widhalm@univie.ac.at

Abstract

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Abstract

A rational strategy for accessing tetrahydroxy compounds in predictable stereoselective fashion from di-O-benzyl protected tartrate is presented. Up to four different aromatic, aliphatic, and vinyl substituents could be stepwise introduced at C1 and C4. This is exemplified in an economic preparation of eight dihydroxy compounds from natural tartaric acid in six steps and 19–59% overall yield. A final deprotection step afforded the corresponding tetrahydroxy compounds in good yields.

Key words

regioselectivity - diastereoselectivity - diols - nucleophilic addition - Grignard reaction

Full Text

References

References

1a Diaz L, Delgado A. Curr. Med. Chem. 2010; 17: 2393
1b Lopez MD, Cobo J, Nogueras M. Curr. Org. Chem. 2008; 12: 718
1c Varela O, Orgueira HA. Adv. Carbohydr. Biochem. 2000; 55: 137

2a Li W, Zhang Z, Xiao D, Zhang X. J. Org. Chem. 2000; 65: 3489
2b Yan Y.-Y, RajanBabu TV. J. Org. Chem. 2000; 65: 900
2c Bayer A, Murszat P, Thewalt U, Rieger B. Eur. J. Inorg. Chem. 2002; 2614

3 Approximate price for (l)-(+)-tartaric acid: € 620 per 20 kg (Acros).

4a Gawroński J, Gawrońska K. Tartaric and Malic Acids in Synthesis . Wiley; New York: 1999
4b Prasad KR, Gandi VR. Tetrahedron: Asymmetry 2011; 22: 499
4c Chavan SP, Harale KR, Dumare NB, Kalkote UR. Tetrahedron: Asymmetry 2011; 22: 587
4d Giovannini R, Marcantoni E, Petrini M. J. Org. Chem. 1995; 60: 5706

5a Ito YN, Ariza X, Beck AK, Bohac A, Ganter C, Gawley RE, Kuehnle FN. M, Tuleja J, Wang YM, Seebach D. Helv. Chim. Acta 1994; 77: 2071
5b Haase C, Sarko CR, DiMare M. J. Org. Chem. 1995; 60: 1777

6a Seebach D, Beck AK, Heckel A. Angew. Chem. Int. Ed. 2001; 40: 92
6b Pellissier H. Tetrahedron 2008; 64: 10279
6c Lam HW. Synthesis 2011; 2011

7a Nugiel DA, Jakobs K, Worley T, Patel M, Kaltenbach III RF, Meyer DT, Jadhav PK, De Lucca GV, Smyser TE, Klabe RM, Bacheler LT, Rayner MM, Seitz SP. J. Med. Chem. 1996; 39: 2156
7b Symmetrical diketones have been also obtained from tartaric acid dichloride: Babudri F, Fiandanese V, Marchese G, Punzi A. J. Organomet. Chem. 2004; 689: 326

8a Prasad KR, Chandrakumar A. Tetrahedron: Asymmetry 2005; 16: 1897
8b Prasad KR, Chandrakumar A. Synthesis 2006; 2159

TADDOL based phosphites, phosphonites, and phosphoramidites have been extensively studied in asymmetric catalysis; usually only P–O–R, P–R, and P–NR₂ parts have been varied, see:

9a Mewald M, Weickgenannt A, Fröhlich R, Oestreich M. Tetrahedron: Asymmetry 2010; 21: 1232
9b Alexakis A, Burton J, Vastra J, Benhaim C, Fournioux X, van den Heuvel A, Levêque J.-M, Mazé F, Rosset S. Eur. J. Org. Chem. 2000; 4011
9c Naeemi Q, Dindaroglu M, Kranz DP, Velder J, Schmalz H.-G. Eur. J. Org. Chem. 2012; 1179

10a Mahalingam SM, Krishnan H, Pati HN. J. Chil. Chem. Soc. 2009; 54: 89 ; Chem. Abstr. 2009, 151, 402658
10b Ahn M, Pietersma AL, Schofield LR, Parker EJ. Org. Biomol. Chem. 2005; 3: 4046

11 A similar selectivity, albeit less pronounced, was observed for 3: McNulty J, Grunner V, Mao J. Tetrahedron Lett. 2001; 42: 5609

For recent applications of tartrate derived auxiliaries in catalysis, see:

12a Waser M, Gratzer K, Herchl R, Müller N. Org. Biomol. Chem. 2012; 10: 251
12b Seki C, Hirama M, Hutabarat ND. M. R, Takada J, Suttibut C, Takahashi H, Takaguchi T, Kohari Y, Nakano H, Uwai K, Takano N, Yasui M, Okuyama Y, Takeshita M, Matsuyama H. Tetrahedron 2012; 68: 1774
12c Hong K, Morken JP. J. Org. Chem. 2011; 76: 9102
12d Teller H, Flügge S, Goddard R, Fürstner A. Angew. Chem. Int. Ed. 2010; 49: 1949
12e Fernández E, Pietruszka J, Frey W. J. Org. Chem. 2010; 75: 5580
12f Liu Z, Du H. Org. Lett. 2010; 12: 3054
12g Robert T, Abiri Z, Wassenaar J, Sandee AJ, Romanski S, Neudörfl J.-M, Schmalz H.-G, Reek JN. H. Organometallics 2010; 29: 478
12h Sokeirik YS, Hoshina A, Omote M, Sato K, Tarui A, Kumadaki I, Ando A. Chem. Asian J. 2008; 3: 1850
12i Garrett MR, Tarr JC, Johnson JS. J. Am. Chem. Soc. 2007; 129: 12944
12j Okada A, Shibuguchi T, Ohshima T, Masu H, Yamaguchi K, Shibasaki M. Angew. Chem. Int. Ed. 2005; 44: 4564

13 Beck AK, Gysi P, Veccia L, Seebach D. Org. Synth. Coll. Vol. 10 . Wiley; London: 2004. 34
14 Love BE, Jones E. J. Org. Chem. 1999; 64: 3755
15 CCDC 890449 contains the supplementary crystallographic data for compound 17 described in this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033, E-mail: deposit@ccdc.cam.ac.uk].
16 Wang ZM, Sharpless KB. Tetrahedron Lett. 1993; 34: 8225
17 Shan ZX, Hu XY, Zhou Y, Peng XT, Li Z. Helv. Chim. Acta 2010; 93: 497