Advances in the Use of Synthons in Organic Chemistry: A by Alessandro Dondoni

By Alessandro Dondoni

Advances within the Use of Synthons in natural Chemistry: A study Annual, quantity 1 offers details pertinent to an invaluable reagent that may practice a undeniable chemical operation that's in a different way most unlikely or tough to hold out. This e-book provides the advancements on validated synthons. geared up into 4 chapters, this quantity starts with an summary of the numerous position of the formyl staff in man made methodologies, which has encouraged the quest for different reagents. this article then describes trimethysilyldiazomethane as a strong and secure replacement for dangerous diazomethane. different chapters think of the usefulness of trimethysilyldiazomethane in natural syntheses. This booklet discusses to boot that malonic amides, silylenol ethers, malonic esters, and tetra-donor-substituted allenes function artificial equivalents for the dianions of malonic esters, ketones, and malonic amides. the ultimate bankruptcy offers with the synthesis of biologically-active compounds, which has been one of many significant demanding situations for natural chemists. This ebook is a priceless source for practising artificial chemists.

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Fogagnolo, M. , Tetrahedron 43 (1987) 3533. , Fogagnolo, M. , Angew. , Int. Ed. Engl. 25 (1986) 835. , Fogagnolo, M. , J. Chem. S o c , Chem. Comm. , Fogagnolo, M. , J. Org. Chem. 55 (1990) 1439. , Orduna, J. , Synthesis (1992) 201. , Medici, A. , J. Org. Chem. 54 (1989) 202. [87] Here we use the term electrophilic formylation to indicate any reaction involving an electrophilic formylating agent in opposition to the umpoled nucleophilic formylation. In some papers (see reference [2], for example), the terms electrophilic- and nucleophilic-formylation are used to differentiate between acid-catalyzed reactions of hydrocarbons with formylating agents and reactions with reagents capable of formylating typical nucleophiles, such as Grignard compounds and alkyllithiums.

Diketene was also employed as a carbon nucleophile, in place of the silyl enol ethers, in the TiCU-promoted reaction with trimethyl orthoformate, affording exclusively y-dimethoxymethyl acetoacetate [128]. In addition to acyclic trialkyl orthoformates, some 2-alkoxy-l,3-dioxanes were used for the preparation of a-dioxanyl ketones from silyl enol ethers, in the presence of ZnCh [129]. Silyl dienol ethers, derived from a,(3-unsaturated aldehydes [130] and ketones [131,132], reacted with orthoformates with complete regioselectivity in the y-position, as was similarly observed for 2-(trimethylsilyloxy)furan 94 [133] (Scheme 46).

Compounds bearing an electron-withdrawing group usually gave very poor yields. Regioselective orf/10-formylation of phenols, via the corresponding 1,3-dithianes was achieved by reaction with a mixture of 1,3-dithiane and Af-chlorosuccinimide [95]. In earlier work, where 75 was characterized as an intermediate, selective p^fm-dithianylation of phenol and dimethylaniline was reported [91b]. However, the yields were low in both cases. Nucleophilic allylic compounds proved to be reactive with 75. The allyl aluminum reagents 76 (Scheme 39), derived from the corresponding allyl bromides [96], gave the 2-alken-2-yl-l,3-dithianes 77a.

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