Direct Synthesis of Medium-Bridged Twisted Amides via a Transannular Cyclization Strategy
نویسندگان
چکیده
منابع مشابه
Synthesis of the macrolactone core of (+)-neopeltolide by transannular cyclization.
The synthesis of the macrolactone core of (+)-neopeltolide has been achieved. The key synthetic strategy involves the highly diastereoselective synthesis of the 2,6-cis-disubstituted tetrahydropyran ring by a transannular cyclization of δ-hydroxy alkene using mercuric trifluoroacetate. Two of the six stereocenters C-5 and C-11 were realized from L-malic acid, while the remaining stereocenters C...
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A crystalline triply bridged molecular gyroscope has been prepared and analyzed by single-crystal X-ray diffraction. A convergent synthetic strategy was developed to control the direction of the three bridges, from the preferred two zonal and one meridional arrangement of a one-step cylclization process to the directed three meridional bridges achieved by a north-south desymmetrization.
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A novel synthesis of anhydrides from twisted amides is reported. Sc(OTf)3 catalysis in the presence of water is used to synthesize anhydrides in one step from amides without external nucleophiles. Mechanistic studies indicate that the coordination of the catalyst is critical to induce the challenging N-C activation step. This process further highlights the utility of twisted amides in organic s...
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Amide bond formation reactions are among the most important transformations in organic chemistry because of the widespread occurrence of amides in pharmaceuticals, natural products and biologically active compounds. The Beckmann rearrangement is a well-known method to generate secondary amides from ketoximes. However, under the acidic conditions commonly employed, aldoximes RHC=NOH rarely rearr...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2009
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol901449y