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Page 1
Oxa-Michael Addition to alpha,beta-Unsaturated Nitriles: An Expedient Route to gamma-Amino Alcohols and Derivatives.
Guo B, Zijlstra DS, de Vries JG, Otten E. Guo B, et al. ChemCatChem. 2018 Jul 9;10(13):2868-2872. doi: 10.1002/cctc.201800509. Epub 2018 May 8. ChemCatChem. 2018. PMID: 30263082 Free PMC article.
Water addition to alpha,beta-unsaturated nitriles would give facile access to the beta-hydroxy-nitriles, which in turn can be hydrogenated to the gamma-amino alcohols. ...Thus, a variety of molecular scaffolds with a 1,3-relationship between O- and N-f …
Water addition to alpha,beta-unsaturated nitriles would give facile access to the beta-hydroxy-nitriles, which in turn …
Enantioselective Rhodium-Catalyzed Allylic Alkylation of beta,gamma-Unsaturated alpha-Amino Nitriles: Synthetic Homoenolate Equivalents.
Wright TB, Turnbull BWH, Evans PA. Wright TB, et al. Angew Chem Int Ed Engl. 2019 Jul 15;58(29):9886-9890. doi: 10.1002/anie.201900442. Epub 2019 Jun 6. Angew Chem Int Ed Engl. 2019. PMID: 30957357
An enantioselective rhodium-catalyzed allylic alkylation of beta,gamma-unsaturated alpha-amino nitriles is described. This protocol provides a novel approach for the construction of beta-stereogenic carbonyl derivatives via the catalytic asymmetric alkylation …
An enantioselective rhodium-catalyzed allylic alkylation of beta,gamma-unsaturated alpha-amino nitriles is described. T …
Hydroxynitrile glucosides.
Bjarnholt N, Møller BL. Bjarnholt N, et al. Phytochemistry. 2008 Jul;69(10):1947-61. doi: 10.1016/j.phytochem.2008.04.018. Epub 2008 Jun 6. Phytochemistry. 2008. PMID: 18539303
We designate these as CYP71(betagamma) and CYP71(alphabetagamma); in combination with the classical CYP71(alpha) (CYP71E1 and orthologs) these are able to hydroxylate any of the carbon atoms present in the amino acid and oxime derived nitriles. Subsequent dehydratio …
We designate these as CYP71(betagamma) and CYP71(alphabetagamma); in combination with the classical CYP71(alpha) (CYP71E1 and orthologs) the …
Synthesis of chiral lactams via asymmetric hydrogenation of alpha,beta-unsaturated nitriles.
Kong D, Li M, Zi G, Hou G. Kong D, et al. Org Biomol Chem. 2016 Apr 26;14(17):4046-53. doi: 10.1039/c6ob00310a. Org Biomol Chem. 2016. PMID: 27056402
A highly efficient Rh-catalyzed enantioselective hydrogenation of alpha,beta-unsaturated nitriles containing ester/amide groups has been developed. Under mild conditions, with a complex of rhodium and (S,S)-f-spiroPhos as the catalyst, a variety of alpha,beta-uns …
A highly efficient Rh-catalyzed enantioselective hydrogenation of alpha,beta-unsaturated nitriles containing ester/amide group …
Asymmetric bioreduction of activated alkenes to industrially relevant optically active compounds.
Winkler CK, Tasnádi G, Clay D, Hall M, Faber K. Winkler CK, et al. J Biotechnol. 2012 Dec 31;162(4):381-9. doi: 10.1016/j.jbiotec.2012.03.023. Epub 2012 Apr 4. J Biotechnol. 2012. PMID: 22498437 Free PMC article. Review.
Ene-reductases from the 'Old Yellow Enzyme' family of flavoproteins catalyze the asymmetric reduction of various alpha,beta-unsaturated compounds at the expense of a nicotinamide cofactor. They have been applied to the synthesis of valuable enantiopure products, including …
Ene-reductases from the 'Old Yellow Enzyme' family of flavoproteins catalyze the asymmetric reduction of various alpha,beta-unsaturated …
P[N(i-Bu)CH(2)CH(2)](3)N: nonionic Lewis base for promoting the room-temperature synthesis of alpha,beta-unsaturated esters, fluorides, ketones, and nitriles using Wadsworth-Emmons phosphonates.
Chintareddy VR, Ellern A, Verkade JG. Chintareddy VR, et al. J Org Chem. 2010 Nov 5;75(21):7166-74. doi: 10.1021/jo1012515. J Org Chem. 2010. PMID: 20945858
The bicyclic triaminophosphine P(RNCH(2)CH(2))(3)N (R = i-Bu, 1c) serves as an effective promoter for the room-temperature stereoselective synthesis of alpha,beta-unsaturated esters, fluorides, and nitriles from a wide array of aromatic, aliphatic, heterocyclic, and …
The bicyclic triaminophosphine P(RNCH(2)CH(2))(3)N (R = i-Bu, 1c) serves as an effective promoter for the room-temperature stereoselective s …
[The chemistry of pericyclic reactions and their application to syntheses of heterocyclic compounds].
Sakamoto M, Kawasaki T, Ishii K, Tamura O. Sakamoto M, et al. Yakugaku Zasshi. 2003 Sep;123(9):717-59. doi: 10.1248/yakushi.123.717. Yakugaku Zasshi. 2003. PMID: 14513766 Free article. Review. Japanese.
Although alpha-alkoxycarbonylnitrones 64 have been very attractive nitrones for the syntheses of amino acids, the nitrones 64 exist as equilibrating mixtures of (E)-64 and (Z)-64. ...These methods were applied to syntheses of nikkomycins, clavalanine, and beta-substituted …
Although alpha-alkoxycarbonylnitrones 64 have been very attractive nitrones for the syntheses of amino acids, the nitrones 64 exist a …
Geometry-Retentive C-Alkenylation of Lithiated alpha-Aminonitriles: Quaternary alpha-Alkenyl Amino Acids and Hydantoins.
Mas-Roselló J, Hachisu S, Clayden J. Mas-Roselló J, et al. Angew Chem Int Ed Engl. 2017 Aug 28;56(36):10750-10754. doi: 10.1002/anie.201704908. Epub 2017 Jul 31. Angew Chem Int Ed Engl. 2017. PMID: 28649795
alpha-Amino nitriles tethered to alkenes through a urea linkage undergo intramolecular C-alkenylation on treatment with base by attack of the lithionitrile derivatives on the N'-alkenyl group. ...The reaction, formally a nucleophilic substitution at an sp(2) carbon …
alpha-Amino nitriles tethered to alkenes through a urea linkage undergo intramolecular C-alkenylation on treatment with base b …
The pyridoxal-phosphate-dependent enzymes exclusively catalyzing reactions of beta-replacement.
Braunstein AE, Goryachenkova EV. Braunstein AE, et al. Biochimie. 1976;58(1-2):5-17. doi: 10.1016/s0300-9084(76)80351-3. Biochimie. 1976. PMID: 782560 Review.
Thus, it appears highly improbable that transient formation of an alphabeta-unsaturated, coenzyme-substrate imine, considered as an obligatory step in the action of lyases in the alphabeta-eliminating and other subgroups, should occur in the sequences of reaction intermedi …
Thus, it appears highly improbable that transient formation of an alphabeta-unsaturated, coenzyme-substrate imine, considered as an o …
58 results