Alpha-Hydroxy Acids in Enantioselective Syntheses by Gary M. Coppola

By Gary M. Coppola

Awareness man made chemist! Chiral alpha-hydroxy acids on hand from nature's chiral pool function beginning fabrics in a wide selection of enantioselective conversions resulting in commercially very important items. This monograph, a stimulating resource of rules and a necessary reference paintings for learn chemists, makes a speciality of the well known lactic, mandelic, malic, and tartaric acids. Well-chosen examples convey how chiral facilities inherent in those basic compounds can be utilized to regulate the advent of extra stereogenic facilities. Readers can at once practice new adjustments of their personal paintings seeing that response stipulations are given in convenient tables.

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3 O-Acyl Lactates The presence of an acyl group on the oxygen of lactic acid derivatives allows chemical manipulations to be performed that would otherwise not be feasible with the corresponding unsubstituted analogs. In addition, the functional groups may be used as synthetic "handles" for further transformations. 1. An example of this strategic approach is a six step synthesis of (S)-( — )-ipsenol (207), a constituent of the sex pheromone of the bark beetle, which is outlined in Scheme 29 [75].

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 [96].

The necessary 2-(ethylthio)allyl silyl ether 414 is prepared in good yield from 402 by conversion to thioester 413 followed by treatment with Tebbe reagent. Reaction of 414 with a variety of aldehydes in the presence of Me2AlCl produces adducts 415 in high yield. To 56 1 Lactic Acid OTBS OTBS OTBS CH2=CHLi THF, -90 °C 73% 401 404 403 OH toluene, -20 °C 405 406 407 Scheme 55 obtain high ee values, the use of non-polar solvents is important. The adduct derived from 2-OTBS benzaldehyde (entry 4) is a useful precursor for the synthesis of optically active anthracyclines.

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