126918-20-5Relevant articles and documents
Enantioselective Construction of Tertiary C-O Bond via Allylic Substitution of Vinylethylene Carbonates with Water and Alcohols
Khan, Ajmal,Khan, Sardaraz,Khan, Ijaz,Zhao, Can,Mao, Yuxue,Chen, Yan,Zhang, Yong Jian
supporting information, p. 10733 - 10741 (2017/08/15)
An efficient method for the enantioselective construction of tertiary C-O bond via asymmetric allylic substitution of racemic vinylethylene carbonates with water and alcohols has been developed. Under the cooperative catalysis system of an in situ generated chiral palladium complex and boron reagent in mild conditions, the process allowed rapid access to valuable tertiary alcohols and ethers in high yields with complete regioselectivities and high enantioselectivities. This protocol represented the first example of direct enantioselective formation of a tertiary C-O bond with water as an oxygen donor. The synthetic utilities of the process have been demonstrated by the elaboration of the products into key intermediates of biologically relevant agents, and chiral tertiary cyclic ethers could also be provided through the sequential reactions of the allylic etherification and ring-closing metathesis.
Preparation method and application of chiral tertiary alcohol or tertiary ether compound
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Paragraph 0186; 0187, (2017/12/27)
The invention discloses a preparation method and application of a chiral tertiary alcohol or tertiary ether compound. A racemase 4-substituted-4-vinyl-1,3-dioxolan-2-one compound is used as a raw material, and under the catalysis of a palladium coordination compound, which is generated under a palladium source and the coordination action of a chiral ligand, and a boron compound which serve as catalysts, reacts with water or alcohol to prepare the chiral tertiary alcohol or tertiary ether compound. The chiral compound provided by the invention is the multi-functionalized chiral tertiary alcohol or tertiary ether compound, can be used for flexibly and conveniently carrying out functional conversion, is about to be an important chiral molecular building block for preparing a chiral drug and an intermediate. The preparation method provided by the invention comprises asymmetric hydroxylation and etherification reactions co-catalyzed by palladium and boron; the preparation method is high in catalytic activity, high in regioselectivity and enantioselectivity and mild in reaction condition; reactive raw materials are conveniently and easily obtained.
Enzyme-catalysed approach to the preparation of triazole antifungals: synthesis of (-)-genaconazole
Acetti, Daniela,Brenna, Elisabetta,Fuganti, Claudio,Gatti, Francesco G.,Serra, Stefano
experimental part, p. 2413 - 2420 (2010/03/24)
The work describes a new enzyme-mediated approach to optically active epoxide (2R,3S)-6, which is an important key intermediate in the preparation of single enantiomers of chiral azole antifungals. The conversion of (2R,3S)-6 into (-)-genaconazole is reported as an example of its synthetic relevance.
Payne rearrangement route to the optically active oxirane precursor for the preparation of triazole antifungals
Konosu,Miyaoka,Tajima,Oida
, p. 562 - 564 (2007/10/02)
Optically active epoxide 1, an important intermediate for the preparation of antifungal triazole-amides 2, was synthesized starting from the (S)-lactic acid-derived ketone 9 and taking advantage of the Payne rearrangement of the epoxyalcohol 8.
Triazole antifungals. III. Stereocontrolled synthesis of an optically active triazolylmethyloxirane precursor to antifungal oxazolidine derivatives
Konosu,Miyaoka,Tajima,Oida
, p. 2241 - 2246 (2007/10/02)
Stereocontrolled synthesis of an optically active triazolylmethyloxirane 2, an important intermediate for the preparation of antifungal oxazolidine compounds 1, was achieved by two methods using L-lactic acid as a starting material. The key intermediate ketone 6 used in the procedures also served for the synthesis of the enantiomer of 2 and the corresponding diastereomeric epoxide.
Triazole derivatives, their preparation and their use as fungicides
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, (2008/06/13)
Compounds of formula (I): in which: Ar is optionally substituted phenyl; R1 is hydrogen or alkyl; X is optionally unsaturated alkylene, cycloalkylene or both; mis 0 or 1; -Yn-R2 is azido, phthalimido, 1-oxo-2,3-dihydro-2-isoindolyl, protected hydroxy or -OSO2R4 (in which R4 is alkyl group, haloalkyl or optionally substituted phenyl); or Y represents a group of formula -N(R5)CO-, -N(R5)CO-CH=CH-, -O-CO-, -O-CO-CH=CH-, -S-CO- or -S-CO-CH=CH- (in which R5 is hydrogen or alkyl); nis 0 or 1; R2 is alkyl, haloalkyl or optionally substituted phenyl, naphthyl or heterocyclic; and R3 is hydrogen; or R3 and -Xm-Yn-R2 together are a group of formula (II): in which R2 is as defined above, pis 0 or 1, and qis 0 or 1;, and acid addition salts thereof are fungicides, which find considerable value in the eradication of fungi in both agriculture and medicine.