Synthesis of Sultam Scaffolds via Intramolecular Oxa-Michael and Diastereoselective Baylis−Hillman Reactions
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چکیده
منابع مشابه
Diastereoselective synthesis of pitavastatin calcium via bismuth-catalyzed two-component hemiacetal/oxa-Michael addition reaction.
An efficient and concise asymmetric synthesis of pitavastatin calcium (1) starting from commercially available (S)-epichlorohydrin is described. A convergent C1 + C6 route allowed for the assembly of the pitavastatin C7 side chain via a Wittig reaction between phosphonium salt 2 and the enantiomerically pure C6-formyl side chain 3. The 1,3-syn-diol acetal motif in 3 was established with excelle...
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An efficient cyclization of 2’-hydroxychalcone to flavanone using calcium chloride as a catalyst was developed. The scope of the reaction was studied with substituted 2’-hydroxychalcone and these chalcones was converted into corresponding flavanone in good yield. The merits of this method are inexpensive and easily available catalyst, easy workup procedure, avoid use of toxic solvent.
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We present a general model for understanding the stereochemical course of intramolecular Michael reactions. We show that the addition of β-ketoester enolates to α,β-unsaturated esters and imides bearing adjacent stereocenters (X, Y = H, Me, OR) leads to high levels of asymmetric induction. Reinforcing and nonreinforcing stereochemical relationships are evaluated from the syn and anti reactant d...
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An asymmetric oxa-Michael/Michael cascade reaction of p-quinols and α,β-unsaturated aldehydes provides access to hindered dialkyl ethers. A highly enantioselective oxa-Michael addition of a tertiary alcohol precedes an intramolecular cyclohexadienone desymmetrization, which allows for the concomitant formation of four contiguous stereocenters in a single step. The highly functionalized bicyclic...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2008
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol8009072