Synthesis, Inhaltsverzeichnis Synthesis 2015; 47(11): 1557-1559DOI: 10.1055/s-0034-1380511 psp © Georg Thieme Verlag Stuttgart · New York Synthesis of (R)-Lactic Acid and (2R,5R)-2-tert-Butyl-5-methyl-1,3-dioxolan-4-one R. Alan Aitken* EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK eMail: raa@st-and.ac.uk , Anna Meehan EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK eMail: raa@st-and.ac.uk , Lynn A. Power EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK eMail: raa@st-and.ac.uk › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A convenient procedure for the synthesis of very expensive (R)-lactic acid from relatively inexpensive (R)-alanine is described. Its subsequent conversion into a chiral dioxolanone can be carried out by using an inexpensive pivalaldehyde–tert-butanol mixture. Key words Key wordschiral pool - stereoselective synthesis - (R)-lactic acid - (R)-alanine - diazotization - 1,3-dioxolan-4-one Volltext Referenzen References 1 Herrmann R. Stereoselective Synthesis. In Houben-Weyl Methods in Organic Chemistry . E21, Vol. 9; Helmchen G, Hoffmann RW, Mulzer J, Schaumann E. Georg Thieme; Stuttgart: 1996: 5910 2 Coppola GM, Schuster HF. α�-Hydroxy Acids in Enantioselective Syntheses . VCH; Weinheim: 1997. Chap. 1, 1-136 3 Brewster P, Hiron F, Hughes ED, Ingold CK, Rao PA. D. S. Nature 1950; 166: 179 4 Strecker A. Justus Liebigs Ann. Chem. 1850; 75: 28 5 Hu DX, O’Brien M, Ley SV. Org. Lett. 2012; 14: 4246 6 Jia C, Yang K.-W, Liu C.-C, Feng L, Xiao J.-M, Zhou L.-S, Zhang Y.-L. Bioorg. Med. Chem. Lett. 2012; 22: 482 7 Raddatz P, Minck K.-O, Rippmann F, Schmitges C.-J. J. Med. Chem. 1994; 37: 486 8 Yang D, Li B, Ng F.-F, Yan Y.-L, Qu J, Wu Y.-D. J. Org. Chem. 2001; 66: 7303 9 Winitz M, Bloch-Frankenthal L, Izumiya N, Birnbaum SM, Baker CG, Greenstein JP. J. Am. Chem. Soc. 1956; 78: 2423 10 Williams PG, Yoshida WY, Moore RE, Paul VJ. J. Nat. Prod. 2002; 65: 29 11 Arimoto H, Oishi T, Nishijima M, Kinumi T. Tetrahedron Lett. 2001; 42: 3347 12 Pitt N, Gani D. Tetrahedron Lett. 1999; 40: 3811 13 Storz T, Dittmar P, Fauquex PF, Marschal P, Lottenbach WU, Steiner H. Org. Process Res. Dev. 2003; 7: 559 14 Leemhuis M, van Steenis JH, van Uxem MJ, van Nostrum CF, Hennink WE. Eur. J. Org. Chem. 2003; 3344 15 Fedushkin IL, Morozov AG, Chudakova VA, Fukin GK, Cherkasov VK. Eur. J. Inorg. Chem. 2009; 4995 16 Seebach D, Naef R, Calderari G. Tetrahedron 1984; 40: 1313 17 Matsuo K, Sakaguchi Y. Chem. Pharm. Bull. 1997; 45: 1620 18a Naef R, Seebach D. Liebigs Ann. Chem. 1983; 1930 18b Boeckman RK. Jr, Yoon SK, Heckendorn DK. J. Am. Chem. Soc. 1991; 113: 9682 18c Kanda Y, Fukuyama T. J. Am. Chem. Soc. 1993; 115: 8451 19 Aitken RA, Thomas AW. Synlett 1998; 102 20 Novikov VL, Shestak OP. Russ. Chem. Bull. Int. Ed. 2013; 62: 2171 21 Kiegiel J, Papis A, Jurczak J. Tetrahedron: Asymmetry 1999; 10: 535
