Preparation of (S)-fluoronitriles

Stelzer, Uwe; Effenberger, Franz

doi:10.1016/s0957-4166(00)82327-7

Cited by 38 publications

(21 citation statements)

References 25 publications

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“…Homochiral cyanohydrins are of synthetic interest as they may be elaborated into a number of key functional groups, including α‐hydroxyacids,4 α‐hydroxyketones,5, 6 primary7–9 and secondary10–12 β‐hydroxyamines, α‐aminonitriles,13 α‐hydroxyesters,14 α‐sulfonyloxynitriles,15 α‐fluoronitriles,16 3‐amino‐2‐trimethylsilyloxy‐2‐alkenoates,17 2,3‐substituted piperidines,18 and azacycloalkan‐3‐ols19 under conditions that conserve high optical purity. Many of these intermediates can be used in further stereoselective transformations.…”

Section: Introductionmentioning

confidence: 99%

Chemically Catalyzed Asymmetric Cyanohydrin Syntheses

Brunel¹,

2004

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Over the past two decades, significant advances have been made towards developing chemically catalyzed asymmetric cyanohydrin syntheses. Preparations that were classically highly substrate specific, often using stoichiometric quantities of reagents, have been revolutionized by a new generation of catalysts. Methods currently available rival, and in many cases surpass, enzymatic procedures in terms of synthetic utility, generic applicability, and enantioselectivity. Such protocols are increasingly finding application in the syntheses of both biologically active natural products and therapeutically important synthetic compounds.

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Section: Introductionmentioning

confidence: 99%

Chemically Catalyzed Asymmetric Cyanohydrin Syntheses

Brunel¹,

2004

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“…According to the sequence rule, a change in the priorities of substituents changes the absolute configuration of the stereogenic center even without its participation in a reaction. It is well established that the fluorinating reagents, particularly DAST, replace the hydroxy group with fluorine stereospecifically to produce a product of inverted configuration with the highest optical purity (28)(29)(30). Compound 4 might have the inversion of an R-to S-configuration at C-12 to which the fluorine is bonded.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and in vitro cytotoxic activity of N‐, F‐, and S‐ether derivatives of podophyllotoxin fatty acid adducts

Mustafa

Khan

et al. 2005

Lipids

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This paper represents the first synthesis, spectroscopic characterization, and antitumor evaluation of F-, N-, and S-containing C4alpha-FA derivatives of podophyllotoxin. In a synthetic strategy, a FA unit of 4-O-podophyllotoxinyl 12-hydroxyoctadec-Z-9-enoate 2, a derivative of podophyllotoxin, was functionalized at the C-12 position by incorporating the F atom and N-containing moieties. The FA olefin (Z, C-9/C-10) of 2 was hydrogenated to produce a derivative possessing a hydroxy function (C-12) on a saturated C18 FA chain. In another synthetic strategy, two S-ethers of podophyllotoxin (C4alpha) were synthesized from a terminal unsaturated FA analog, 4-O-podophyllotoxinyl undec-10-enoate. Syntheses were achieved through effective synthetic procedures; 1H NMR, 13C NMR, IR, and high-resolution mass data proved excellent tools to characterize these derivatives. In vitro antitumor activity was investigated against a panel of five human neoplastic cell lines, SK-MEL (malignant, melanoma), KB (epidermal carcinoma, oral), BT-549 (ductal carcinoma, breast), SK-OV-3 (ovary carcinoma), and HL-60 (human leukemia). Keeping in view the severe lack of tumor selectivity of podophyllotoxin over normal cells, we assayed new analogs against noncancerous mammalian VERO (African green monkey kidney fibroblast) cell lines to gauge their extent of toxicity. Several of these compounds showed excellent moderation of antitumor activity. In general, we found excellent growth inhibition against the human leukemia cell line (HL-60), particularly for the analogs containing S-ethers and carbamates. None of the compounds were toxic to normal cell lines.

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“…They can easily be prepared by the addition of cyanide to a carbonyl compound in the presence of a synthetic chiral catalyst or an enzyme (Scheme 2). The resulting cyanohydrins are readily transformed into a variety of compounds such as a-hydroxyacids [102], a-aminoacids [103][104][105][106][107][108][109][110][111][112], a-hydroxyaldehydes, a-hydroxyketones [113,114], b-aminoalcohols, among others [115][116][117][118][119][120][121][122][123][124][125][126][127]. Despite the immense synthetic potential offered by chiral cyanohydrins in the synthesis of bio-active molecules, it is surprising that intensive research on this topic has started relatively recently.…”

Section: Asymmetric Cyanation Reactionmentioning

confidence: 99%

Dimeric & Polymeric Chiral Schiff Base Complexes and Supported BINOL Complexes as Potential Recyclable Catalysts in Asymmetric Kinetic Resolution and C–C Bond Formation Reactions

et al. 2009

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This review is based on dimeric and polymeric chiral Schiff base metal complexes and chiral BINOL supported metal complexes as potential recyclable catalysts for kinetic resolution of racemic and meso epoxide and asymmetric C-C bond formation reactions e.g., asymmetric addition of diethylzinc to aldehydes, enantioselective addition of phenylacetylene to aldehydes, asymmetric nitro-Aldol reactions and asymmetric cyanation reaction.

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Preparation of (S)-fluoronitriles

Cited by 38 publications

References 25 publications

Chemically Catalyzed Asymmetric Cyanohydrin Syntheses

Chemically Catalyzed Asymmetric Cyanohydrin Syntheses

Synthesis and in vitro cytotoxic activity of N‐, F‐, and S‐ether derivatives of podophyllotoxin fatty acid adducts

Dimeric & Polymeric Chiral Schiff Base Complexes and Supported BINOL Complexes as Potential Recyclable Catalysts in Asymmetric Kinetic Resolution and C–C Bond Formation Reactions

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