Carbon-carbon bond formation via the reaction of trialkylallylstannanes with organic halides

Keck, Gary E.; Yates, John B.

doi:10.1021/ja00385a066

Cited by 275 publications

(90 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[21] The synthesis of the carbocyclic nucleosides 5 and 6 started with the activation of the 3Ј-hydroxy group in the protected carba-dT derivative 13 by reaction with phenoxythiocarbonyl chloride (PTC-Cl). [22] The resulting thiocarbonate 18 was isolated in 95 % yield (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antiviral Evaluation of Carbocyclic 3′‐Azidothymidine (AZT) Analogues and Their cycloSal‐Phosphate Triesters

Ludek¹,

Balzarini²,

Meier³

2006

Eur J Org Chem

View full text Add to dashboard Cite

Carbocyclic analogues of the anti‐HIV dideoxynucleoside 3′‐azido‐3′‐deoxythymidine AZT (1) were synthesized. Starting from the enantiomerically pure carbocyclic 2′‐deoxythymidine 2, four different carbocyclic AZT analogues 2,4–6 were prepared. Moreover, the nucleoside analogues were converted into their membrane‐permeable cycloSal‐phosphate triesters. All compounds were tested in vitro for their anti‐HIV activity in human T‐lymphocytes (CEM/0). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and Antiviral Evaluation of Carbocyclic 3′‐Azidothymidine (AZT) Analogues and Their cycloSal‐Phosphate Triesters

Ludek¹,

Balzarini²,

Meier³

2006

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…In the eighties, Keck and Migita showed that the allylation of organic halides with allyltri-n-butylstannane pro-vided a powerful and selective synthetic method for introducing allyl groups [18][19][20] . The reactions of allyltri-n-butylstannane with alkyl halides, especially with polyhaloalkanes, a-haloesters or a-halonitriles took place under mild conditions in excellent yields.…”

Section: Displacement Of the Bromine By Allyl End Groupsmentioning

confidence: 99%

“…3) End functionalization by radical addition reactions was demonstrated to be applicable to polymers with multiple halogen end groups, such as hyperbranched and star polymers. Hyperbranched poly(2,2-bromopropionyloxy)ethyl acrylate (pBPEA) (Scheme 4) was synthesized by ATRP as described before 18) . Three-armed star poly(methyl acrylate) was prepared by ATRP using a trifunctional initiator, 1,1,1-tris(2-bromoisobutyryloxy)phenylethane, in combination with CuBr/4,49-di-tert-butyl-2,29-bipyridine as catalyst (Scheme 5).…”

Section: Displacement Of the Bromine By Allyl End Groupsmentioning

confidence: 99%

Functionalization of polymers prepared by ATRP using radical addition reactions

Coessens

Pyun

Miller

et al. 2000

Macromol. Rapid Commun.

109

View full text Add to dashboard Cite

“…Thus, hydrolysis of the methyl ester with LiOH followed by treatment with iodine gave iodolactone 93 in 60 % yield. Subsequent Keck allylation with allyltributyl-stannane [73] using the Hart/Wipf protocol74 furnished 94 in 62 % yield and with excellent diastereoselectivity. Johnson-Lemieux oxidation of the allyl group afforded the expected aldehyde 95 which was treated with 1,2-ethanedithiol and BF 3 ؒEt 2 O to give 96 in 48 % yield for both steps.…”

Section: Synthesis Of Complex Polyazacyclic Systems By the Imdaf Reacmentioning

confidence: 99%

Tandem Methodology for Heterocyclic Synthesis

Padwa

2005

ChemInform

View full text Add to dashboard Cite

Tandem methodology for heterocyclic synthesis represents a powerful approach for the rapid buildup of molecular complexity from potentially simple starting materials. Work from our laboratory has shown that the rhodium(II)-catalyzed cyclization cascade of α-diazo imides represents an effective method for the synthesis of a variety of heterocyclic systems. As an extension of these studies, we became interested in using a linked Pummerer/N-acyliminium ion cyclization sequence since we felt that this combination offers unique opportunities for the assemblage of complex target molecules. A synthetic method that combines transformations of different reaction types significantly broadens the scope of such procedures in synthetic chemistry. α-Thiocarbocations generated from the Pummerer reaction of β-phenylsulfinylmethyl-α,β-unsaturated amides can be intercepted by the adjacent amido group to produce transient amino-substituted furans which undergo subsequent Diels-Alder cycloadditions. Using this domino amido Pummerer/Diels-Alder cascade, we were able to assemble novel polycyclic systems in a single operation. The key step in the process involves the generation of a reactive N-acyliminium ion by fragmentation of an amino-substituted [4+2]-cycloadduct. The successful synthesis of a number of alkaloids by this sequence of reactions reveals the usefulness and importance of this unique domino cascade. Application of the process for the preparation of the stenoma alkaloid stenine was recently carried out in our laboratory.

show abstract

Carbon-carbon bond formation via the reaction of trialkylallylstannanes with organic halides

Cited by 275 publications

References 0 publications

Synthesis and Antiviral Evaluation of Carbocyclic 3′‐Azidothymidine (AZT) Analogues and Their cycloSal‐Phosphate Triesters

Synthesis and Antiviral Evaluation of Carbocyclic 3′‐Azidothymidine (AZT) Analogues and Their cycloSal‐Phosphate Triesters

Functionalization of polymers prepared by ATRP using radical addition reactions

Tandem Methodology for Heterocyclic Synthesis

Contact Info

Product

Resources

About