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Showing papers in "Tetrahedron Letters in 1983"


Journal ArticleDOI
TL;DR: In this article, new phosphonoester reagents and reaction conditions are described which yield Z-alpha, beta-unsaturated esters stereoselectively and in high yield from aliphatic and aromatic aldehydes.

924 citations


Journal ArticleDOI
TL;DR: In this article, various deoxynucleoside N,N-dialkylaminomethoxyphosphines were examined for stability and reactivity in deoxyoligonucleotide synthesis.

556 citations


Journal ArticleDOI
TL;DR: In this article, a new template-based strategy was developed for synthesizing catenanes, based on a generalized template effect, as shown in Figure 1, and the first example of a novel class of molecules, the metallo-catenanes, has been obtained in good yield: it contains copper and macrocyclic phenanthroline derivatives.

550 citations


Journal ArticleDOI
TL;DR: Alkynyl boranes, generated in situ from lithium acetylides and boron trifluoride etherate, were found to react with oxiranes under mild reaction conditions to afford β-hydroxyacetylenes in high yields.

395 citations



Journal ArticleDOI
TL;DR: In this article, β-Cyanoethyl monochlorophosphoamidites of the secondary amines N, N-dmethylamine, N,N-diisopropylamine and morpholine have been prepared which showed quantitative phosphitylation of the protected deoxynucleosides.

279 citations


Journal ArticleDOI
TL;DR: C-acylation of lithium enolates by methyl cyanoformate provides high yields of β-keto esters under mild conditions and with 100% regioselectivity as mentioned in this paper.

266 citations


Journal ArticleDOI
Kazuhiko Takai1, Keizo Kimura1, Tooru Kuroda1, Tamejiro Hiyama1, Hitosi Nozaki1 
TL;DR: Alkenyl iodide (or bromide) is readily reduced with CrCl2 is N,N-dimethylformamide at 25°C to gice the corresponding organochromium species which adds selectively to an aldehyde moiety without affecting the coexisting ketone or cyano group of the substrate.

264 citations


Journal ArticleDOI
TL;DR: Enol triflates can be prepared in high yield from regiospecific generated enolates by trapping with N-phenyltrifluoromethanesulfonimide.

260 citations


Journal ArticleDOI
TL;DR: A general chemoselective method for the reduction of azides into primary amines was described in this article, where the reduction was carried out by using a general method for azides.

237 citations


Journal ArticleDOI
TL;DR: The reaction of organozincs with acyl chlorides catalyzed by palladium-phosphine complexes, e.g., Pd(PPh 3 ) 4, provides a highly general and convenient route to ketones as mentioned in this paper.

Journal ArticleDOI
TL;DR: Samarium diiodide is an excellent reagent for aldehyde or ketone coupling as mentioned in this paper, and reactions are very fast with a complete selectivity versus substituents such as cyano, carboxyl or nitro groups.

Journal ArticleDOI
TL;DR: In this article, a new method for five-membered ring annulation is described which involves free radical generation from ketones by zinc-trimethylchlorosilane followed by internal addition to a π-bond.

Journal ArticleDOI
TL;DR: In this article, the intermolecular Diels-Alder reactions employing dienophiles 1 and 5 with diene 2 have been examined in water and significantly enhanced rates, as well as the improved selectivity observed in water stand in sharp contrast to the results observed in hydrocarbon solvents.

Journal ArticleDOI
TL;DR: The structure of Pyoverdine Pa, the siderophore of Pseudomonas aeruginosa, was elucidated by degradation, by FAB mass spectrometry and by NMR; it consists of a linear octapeptide bound to a 2,3-diamino-6,7-dihydroxyquinoline derived chromophore as discussed by the authors.

Journal ArticleDOI
TL;DR: In the presence of a hydroxyl group juxtaposed for participation, NaBH(OAC)3 reduced even ketones in a stereo and regiospecific manner and in excellent yields as discussed by the authors.

Journal ArticleDOI
TL;DR: Carboxylic acid esters derived from N-hydroxy-pyridine-2-thione react with carbon tetrachloride, bromotrichloromethane or iodoform in a radical chain reaction to give the corresponding noralkyl chlorides or iodides in high yield.

Journal ArticleDOI
TL;DR: The structure of genotoxic metabolite, streptindole, isolated from intestinal bacteria (Streptococcus faecium IB 37) has been established as 2,2-di(3-indolyl) ethyl acetate by spectroscopic and synthetic methods as discussed by the authors.

Journal ArticleDOI
TL;DR: In this article, the structures of fosfazinomycins A and B, phosphorus containing antibiotics, have been established by spectral evidence and degradation studies, and they have been shown to have similar properties to those of FOSFAS.

Journal ArticleDOI
TL;DR: Acylation of readily available 3-methyl-3-hydroxymethyl oxetane (2) leads to the corresponding Oxetane esters (3 ) which rearrange smoothly in the presence of boron trifluoride etherate in methylene chloride at −15° to form ortho esters of the 2, 6, 7-trioxabicyclo[2.2] octane series (4 ).


Journal ArticleDOI
TL;DR: In this article, it was shown that the oxidation of ketone hydrazones by iodine in the presence of a base to furnish vinyl iodides has been improved by three factors: absence of water, the use of strong guanidine bases and inverse addition.

Journal ArticleDOI
TL;DR: In this article, the structure-stereoselectivity relationship between α-hydroxy ketones and zinc horohydride has been investigated and α-butyldiphenylsilyoxy derivatives with sodium bis(2methoxyethoxy)aluminum hydride gave the isomeric threoglycols.

Journal ArticleDOI
TL;DR: The structure of the lipid A component of E. coli lippopolysaccharide was determined by means of chemical and 2D-NMR methods unequivocally to be a glucosamine β(1′-6)-disaccharide 1,4′-diphosphate acylated at the two hydroxyl (positions C-3 and −3′) and the two amino groups.

Journal ArticleDOI
TL;DR: In this paper, structures for solanapyrones A, B and C, phytotoxins from the fungus Alternaria solani, parasite of potato, were proposed on the basis of spectroscopic data and chemical reaction.

Journal ArticleDOI
TL;DR: In this paper, the X-B moiety was added to CC bonds in a cis fashion to accelerate the bromoboration reaction at terminal CC bonds but not at internal C�C, terminal and internal C�C bonds.

Journal ArticleDOI
TL;DR: In this article, allyl enol carbonates, prepared from ketones or aldehydes by trapping their enolates with allyl chloroformate, to give α-allyl ketones and aldehides regioselectivity is catalyzed by palladium-phosphine complexes under mild conditions.

Journal ArticleDOI
TL;DR: In this article, Nitrobenzaldehyde reacts smoothly with dialkylphosphonates in the presence of catalytic quantities of cinchona alkaloids (e.g. quinine) to produce the α-hydroxy phosphate esters in excellent chemical yields, with excellent enantiomeric enrichment.

Journal ArticleDOI
TL;DR: In this paper, a general stereo-directed synthesis of komethylene and hydroxylene dipeptide isosteres was reported. But the synthesis was performed using a pepstatin with statine replaced by Leu-Ala.

Journal ArticleDOI
TL;DR: In this paper, a practical, stereocontrolled synthesis of leukotriene B5 is described, which makes this substance readily available for the first time and can be used for medical applications.