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By Dieter Enders, Karl-Erich Jaeger, Günter Helmchen

Edited by way of of the prime researchers within the box, this booklet offers a deep, interdisciplinary perception into stoichiometric and catalytic reactions during this regularly increasing zone. A plethora of best German scientists with a global acceptance covers numerous points, from classical natural chemistry to technique improvement, and from the theoretical heritage to organic equipment utilizing enzymes. through the concentration is at the improvement of recent man made equipment in uneven synthesis, the synthesis of usual and bioactive compounds and the most recent advancements in either chemical and organic tools of catalysis, in addition to the research of exact technical and biotechnical facets.

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74 D. A. Evans, A. H. Hoveyda, J. Am. Vignola, G. Raabe, Helv. Chim. Acta Chem. Soc. 1990, 112, 6447. 2002, 85, 3657. 75 S. D. Rychnovsky, G. Griesgraber, S. 91 E. B. Evans, E. E. Mabbott, E. E. Turner, Zeller, D. Skalitzky, J. Org. Chem. 1991, J. Chem. Soc. 1927, 1159. 56, 5161. 92 a) E. J. Corey, K. A. Cimprich, 76 S. D. Rychnovsky, S. S. Swenson, J. Org. Tetrahedron Lett. 1992, 33, 4099; b) Chem. 1997, 62, 1333, and references R. M. Lawrence, S. A. Biller, J. K. cited therein. Dickson, J. V.

By employing a protocol reported by Lipshutz et al. [93] utilizing Pd(OAc)2 in refluxing EtOH/H2O, the sulfonic acids could be obtained. Alternatively, the removal of the auxiliary can be carried out with 2 mol% trifluoroacetic acid (TFA) in ethanol. In order to isolate the final products in a more accessible form, they were directly converted with diazomethane into the corresponding methyl sulfonates 116 in very good yields (77–98%) and as pure stereoisomers (ee > 98%). 31) [94]. Based on this gathered experience the diastereoselective alkylation of enantiopure α -lithiated sulfonates was extended to the Michael addition with aliphatic nitroolefins [95].

ROH, 2. CH2N2 R3 R2 R1 (R,S)-126 (de, ee ≥ 98%) OR 87 - 91% 1. H2O/acetone (1:2) 2. 35 Highly stereoselective synthesis of γ alkoxysulfonates, γ -hyroxysulfonates, and γ -aminosulfonates. i-PrO3S R3 R2 R1 NHBoc (R,S)-128 (de, ee ≥ 98%) References 33 O O H3C H3C O O CH3 O O S 1. 2% TFA/EtOH 2. CH2N2/Et2O O O R 62 - 78% CH3 NO2 1. NaBH4, 10% Pd/C, THF/MeOH, (76%) 2. CbzCl, K2CO3, CH2Cl2/H2O (56%) (R,R)-129 R (de ≥ 98%) CO2Et R SO3CH3 (R,R)-130c (de, ee ≥ 98%) DIBAL/CH2Cl2 NHCbz SO3R* 43 - 84% 95% 1.

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