Enzymatic Resolution of 5‐Phenylselanyltetrahydro‐2‐furanone. Enantioselective Preparation of (R) and (S)‐γ‐Valerolactone

Abstract

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Lipase-catalyzed kinetic resolution of (RS)-hydroxy tellurides

“…The absolute stereochemistry was then determined by comparison of the specific rotation of 10 with the literature data. 21 In this way, the absolute stereochemistry of alcohol 5f was determined as (S).…”

First chemoenzymatic synthesis of organoselenium amines and amides

“…[1][2][3][4][5][6][7][8][9] The constant interest in this area can be devoted to the wide application of selenium to organic synthesis and biological chemistry. For example, we mention that compounds containing a selenium atom have important antioxidant and antiinflammatory activities.…”

A short and efficient enantioselective synthesis of (+) and (-)-(Z)-7,15-hexadecadien-4-olide: the sex pheromone of the yellowish elongate chafer, Heptophylla picea

“…5 Recently we initiated a program aiming at the synthesis of enantiomericaly pure naturally occurring lactones using enzymes in a deracemization step. [6][7][8] A versatile protocol introduced by us consists in the application of a methodology developed by Gutmam and coworkers, which transforms the commercially available 4-ketopimelic acid (1) into the chiral lactone (S)-(-)-2, which was transformed in our laboratory into both (S) 7 and (R) 8 isomers of jasmolactone 3, a compound with organoleptic properties, described as fruity, flowery, green, creamy, sweet and juicy 3 (Scheme 1). This strategy is interesting since the common intermediate 2 can lead to both enantiomers of a naturaly occurring γ-butyrolactone.…”