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Literature DB >> 20459076

Borostannylation of alkynes and enynes. Scope and limitations of the reaction and utility of the adducts.

Ramakrishna Reddy Singidi¹, T V RajanBabu.

Abstract

The utility of the hetero-bismetallating reagent 1,3-dimethyl-2-trimethylstannyl-2-bora-1,3-diazacyclopentane (1) has not been fully realized because of the hydrolytic instability of the products derived from catalyzed vicinal syn-additions to alkynes. The isolation of a variety of such adducts derived from alkynes (and also from hitherto unreported additions to 1,3-enynes) as stable boron pinacolates is reported. Examples of the applications of resulting products in tandem cross-coupling reactions and as dienes in Diels-Alder reactions are illustrated.

Entities: Chemical Disease Gene

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Year: 2010 PMID： 20459076 PMCID： PMC2886519 DOI： 10.1021/ol100824f

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

10 in total

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5. Tandem Stille/Suzuki-Miyaura coupling of a hetero-bis-metalated diene. Rapid, one-pot assembly of polyene systems.

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Journal: Org Lett Date: 2005-05-26 Impact factor: 6.005

6. Total synthesis of 2'-O-methylmyxalamide D and (6E)-2'-O-methylmyxalamide D.

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8. Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling.

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Journal: Org Lett Date: 2009-09-17 Impact factor: 6.005

9. Silylstannylation of allenes and silylstannylation-cyclization of allenynes. Synthesis of highly functionalized allylstannanes and carbocyclic and heterocyclic compounds.

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10. Catalyzed cyclizations leading to enrichment of functionality and chirality. A general approach to dibenzocyclooctadiene lignans from alpha,omega-diynes.

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