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

By Gary M. Coppola

Consciousness 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 vital items. This monograph, a stimulating resource of principles and an important reference paintings for learn chemists, specializes in the well known lactic, mandelic, malic, and tartaric acids. Well-chosen examples exhibit how chiral facilities inherent in those uncomplicated compounds can be utilized to regulate the advent of additional stereogenic facilities. Readers can at once follow new adjustments of their personal paintings on account that response stipulations are given in convenient tables.

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1. 1 Acetyl o O CH3 (S)-2-(Acetyloxy)propanoic Acid L-2-Acetoxypropionic acid (123) is readily prepared by the acylation of L-lactic acid with either acetic acid/sulfuric acid in benzene (50% yield) [79] or with an excess of acetyl chloride (80% yield) [80]. One is not limited exclusively to the use of lactic acid as the starting material. Diazotization of L-alanine in acetic acid furnishes 123 in 47% yield with at least 96% retention of configuration [48]. Esterification of 123 with diazoethane furnishes ethyl (S)-2-acetoxypropionate (222).

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]. LLactic acid is activated through formation of mixed anhydride 203, and subsequent addition of methylmagnesium bromide furnishes methyl ketone 204. Aldol condensation of enol silyl ether 205 with isovaleraldehyde gives the adduct 206 (89% ds).

2 Benzyl CHcT COOH (5)-2-(Phenylmethoxy)propanoic Acid Benzylation of lactic acid esters can be accomplished by two methods. Treatment of methyl or ethyl L-lactate with benzyl bromide and silver oxide provides the corresponding (*S)-2-benzyloxypropionates 271 with high optical purity [92,93]. Use of standard basic conditions (NaH, DMF) results in considerable racemization (50—75% ee). Alternately, ethyl L-lactate can be benzylated without racemization using benzyl trichloroacetimidate [94,95]; however, this reagent is rather expensive.

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