By Gary M. Coppola
Recognition man made chemist! Chiral alpha-hydroxy acids to be had from nature's chiral pool function beginning fabrics in a large choice of enantioselective conversions resulting in commercially very important items. This monograph, a stimulating resource of principles and an important reference paintings for study chemists, specializes in the well known lactic, mandelic, malic, and tartaric acids. Well-chosen examples convey how chiral facilities inherent in those easy compounds can be utilized to manage the advent of extra stereogenic facilities. Readers can without delay practice new ameliorations of their personal paintings on account that response stipulations are given in convenient tables.
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Extra info for Alpha-Hydroxy Acids in Enantioselective Syntheses
5]decane is a pheromone produced by two varieties of bees, Parvespula vulgaris L. and Andrena haemorrhoa F. The 2R, 5R, 7/^-isomer (188) has been synthesized using 147, ultimately derived from ethyl L-lactate, to supply the chiral stereocenter at C-2 (Scheme 26) . The second chiral intermediate 185 is derived from (S)-( — )-malic acid. 6% starting from 184, and the optical purity of the final product is 96%. 4), and the enantiomer of 185, available from (*S)-malic acid. 3 O-(Trifluoromethanesulfonyl) L-Lactic Acid Derivatives OS02CF3 (S)-2-[[(Trifluoromethyl)sulfonyl]oxy]propanoic Acid The enhanced leaving ability of the triflate group allows SN2 substitution reactions to occur at lower temperatures and over shorter periods of time relative to other leaving groups.
MS CH3COSCs J^ CHs H 3% HCI, BOH 90% C 95% 168 156b 169 The properties of cesium salts can be taken advantage of to convert (
Alternately, ethyl L-lactate can be benzylated without racemization using benzyl trichloroacetimidate [94,95]; however, this reagent is rather expensive. (S)-2-Benzyloxylactic acid (274) is accessible in two steps via asymmetric alkylation of glycolic acid derivative 272. Methylation of 272 proceeds in high yield to give 273 with 97% de. H PhCH2Br OCH2Ph Ag2O CH;T 9H CI3C(NH)OCH2Ph COOR TFA (cat) 63% CH3" 69% 271 a R = CH3 271b R= B 2 triflate can also be used to obtain products with greater than 96% de .