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For matching and mismatching effects in the proline-catalyzed aldol reaction of enantiopure aldehydes, see:
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The 3-substituted 3-hydroxy-β-lactam moiety represents an efficient carboxylate mimic, see:
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The 3-substituted 3-hydroxy-β-lactam moiety is present in several pharmacologically active monobactams such as sulphazecin and related products, see:
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The 3-substituted 3-hydroxy-β-lactam moiety is present in enzyme inhibitors such as tabtoxin and its analogues. See:
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Some 3-substituted 3-hydroxy-β-lactams showed promising activity in acyl CoA-cholesterol acyltransferase inhibition assays, see:
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33847663354
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Isoserines are key components of a large number of therapeutically important compounds. As an example, (2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid (norstatine) and (3R,4S)-4-amino-3-hydroxy-5-methylheptanoic acid (statine) are residues for peptide inhibitors of enzymes, such as renin and HIV-1 protease, see:
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Moreover, phenylisoserine analogues are used to synthesize new taxoids
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59
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33847663353
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For the proline-catalyzed direct aldol reaction of aldehydes with α-keto esters as aldol acceptors, see:
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60
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0002462320
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For the proline-catalyzed asymmetric aldol reaction between cyclohexanone and phenylglyoxylate, see:
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Bøgevig A., Kumaragurubaran N., and Jørgensen K.A. Chem. Commun. (2002) 620 For the proline-catalyzed asymmetric aldol reaction between cyclohexanone and phenylglyoxylate, see:
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For the organo-catalyzed asymmetric direct aldol reaction of acetone with α-keto acids, see:
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Luppi G., Cozzi P.G., Monari M., Kaptein B., Broxterman Q.B., and Tomasini C. J. Org. Chem. 70 (2005) 7418 For the organo-catalyzed asymmetric direct aldol reaction of acetone with α-keto acids, see:
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33847676270
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note
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A typical reaction of azetidine-2,3-diones 1 was catalyzed (10 mol %) by N-benzylglycine and was conducted in acetone for a period of 2 days (conversion up to 5%).
-
-
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65
-
-
33847673619
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note
-
A typical reaction of azetidine-2,3-diones 1 was catalyzed (10 mol %) by glycine and was conducted in acetone for a period of 3 days (yield up to 45%).
-
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66
-
-
33847674031
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note
-
A typical reaction of azetidine-2,3-diones 1 was catalyzed (10-15 mol %) by triethylamine or Hünig's base and was conducted in acetone at room temperature.
-
-
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67
-
-
33847654258
-
-
note
-
A typical reaction of azetidine-2,3-diones 1 was catalyzed (10 mol %) by the system pyrrolidine/acetic acid (1:1) and was conducted in acetone for a period of 24 h. In addition to the aldol product (yield up to 31%), some epimerization on the starting ketone was detected.
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68
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33847613304
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81
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33847674452
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Match implies that the catalyst reinforces the inherent diastereoselectivity of the substrate, and mismatch implies that the catalyst contradicts the inherent diastereoselectivity. With matched catalyst/substrate pairs, the selectivity is universally excellent. Furthermore, in every mismatched case, the catalyst is able to override and control the diastereoselectivity of the addition.
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82
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33847636075
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note
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The use of triethylamine (35 mol %) as promoter instead of N-methylephedrine in the nitroaldol reaction of azetidine-2,3-diones 1 was equally effective, being obtained the corresponding Henry adducts 5 in similar yields.
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83
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0021775497
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For a review on the principles of double- and reagent-controlled stereoselection in the context of the aldol reaction, see:
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For a review on the principles of double- and reagent-controlled stereoselection in the context of the aldol reaction, see:. Masamune S., Choy W., Petersen J.S., and Sita L.R. Angew. Chem., Int. Ed. Engl. 24 (1985) 1
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