1268604-75-6Relevant academic research and scientific papers
Remote Functionalization of α,β-Unsaturated Carbonyls by Multimetallic Sequential Catalysis
Romano, Ciro,Fiorito, Daniele,Mazet, Clément
supporting information, p. 16983 - 16990 (2019/10/28)
The remote functionalization of α,β-unsaturated carbonyls by an array of multimetallic sequential catalytic systems is described. The reactions are triggered by hydrometalation using [Pd-H] or [Ru-H] isomerization catalysts and driven by the formation of thermodynamically more stable 1,2-vinyl arenes. The Pd-catalyzed deconjugative isomerization was combined with a Cu-catalyzed β-borylation of the transiently generated styrenyl derivatives to deliver a range of products that would not be accessible with the use of a single catalyst. [Pd/Cu] catalytic systems were also identified for the highly enantioselective α-hydroboration and α-hydroamination of the styrenyl intermediates. Difunctionalization simultaneously at the benzylic and homobenzylic positions was achieved by combining the isomerization process with Sharpless asymmetric dihydroxylation (SAD) using [Pd/Os] or [Ru/Os] couples. Starting from a simple α,β-unsaturated ester, an isomerization/dihydroxylation/lactonization sequence gave access to a naturally occurring γ-butyrolactone in good yield, with excellent diastereo- and enantioselectivity.
N,N,N′,N′-Tetramethylenediamine dioxide (TMEDAO2) facilitates atom economical/open atmosphere Ley-Griffith (TPAP) tandem oxidation-Wittig reactions
Read, Christopher D. G.,Moore, Peter W.,Williams, Craig M.
supporting information, p. 4537 - 4540 (2015/09/15)
N,N,N′,N′-Tetramethylethylenediamine dioxide (TMEDAO2) was explored as a more atom economical co-oxidant for the Ley-Griffith oxidation of alcohols to aldehydes. TMEDAO2 was found to selectivity oxidise benzylic and allylic alcohols in comparable yields to that of the standard Ley-Griffith co-oxidant (NMO). Importantly TMEDAO2 facilitated tandem Ley-Griffith-Wittig reactions with stabilised ylides, in good to excellent yields, without the requirement of anhydrous conditions.
An expedient stereoselective synthesis of the antifungal agent (6 S)-6-[(2 R)-2-hydroxy-6-phenylhexyl]-5,6-dihydro-2H-pyran-2-one
Narsaiah, A. Venkat,Ghogare, Ramesh S.
experimental part, p. 3271 - 3276 (2011/11/30)
An efficient and straightforward stereoselective synthesis of (6S)-6-[(2R)-2-hydroxy-6-phenylhexyl]-5,6-dihydro-2H-pyran-2-one is described. The chiral centers were generated by Sharpless asymmetric epoxidation followed by regioselective epoxide ring open
Stereoselective total synthesis of (+)-strictifolione and (6R)-6[(E,4R,6R)-4,6-dihydro-10-phenyl-1-decenyl)-5,6-dihydro-2H-2-pyrone
Das, Biswanath,Veeranjaneyulu, Boyapati,Balasubramanyam, Penagaluri,Srilatha, Malampati
experimental part, p. 2762 - 2767 (2011/03/18)
The stereoselective total synthesis of two naturally occurring α-pyrone derivatives, (+)-strictifolione and (6R)-6[(E,4R,6R)-4,6- dihydroxy-10-phenyl-1-decanyl]-5,6-dihydro-2H-2-pyrone has been accomplished involving the Sharpless kinetic resolution and o
