- Highly Enantioselective Iridium-Catalyzed Coupling Reaction of Vinyl Azides and Racemic Allylic Carbonates
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The iridium-catalyzed enantioselective coupling reaction of vinyl azides and allylic electrophiles is presented and provides access to β-chiral carbonyl derivatives. Vinyl azides are used as acetamide enolate or acetonitrile carbanion surrogates, leading to γ,δ-unsaturated β-substituted amides as well as nitriles with excellent enantiomeric excess. These products are readily transformed into chiral N-containing building blocks and pharmaceuticals. A mechanism is proposed to rationalize the chemoselectivity of this coupling reaction.
- Han, Min,Yang, Min,Wu, Rui,Li, Yang,Jia, Tao,Gao, Yuanji,Ni, Hai-Liang,Hu, Ping,Wang, Bi-Qin,Cao, Peng
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supporting information
p. 13398 - 13405
(2020/09/02)
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- A Convenient Palladium-Catalyzed Carbonylative Synthesis of (E)-3-Benzylidenechroman-4-ones
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A convenient palladium-catalyzed carbonylation reaction for the efficient synthesis of (E)-3-benzylidenechroman-4-ones has been developed. Using TFBen as a solid CO source, a range of substituted (E)-3-benzylidenechroman-4-ones were prepared in moderate to good yields with 2-iodophenols and allyl chlorides as the substrates. Additionally, substituted quinolin-4(1H)-ones can also be obtained with 2-iodoaniline as the starting material.
- Wang, Wei-Feng,Peng, Jin-Bao,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
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supporting information
p. 3521 - 3524
(2019/02/14)
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- Manganese(III) acetate mediated oxidative radical cyclizations. Toward vicinal all-carbon quaternary stereocenters
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Manganese(III) acetate mediated oxidative radical cyclizations have been used to synthesize a range of densely functionalized and sterically congested cyclopentane-lactones. A number of the resulting lactones contain vicinal all-carbon quaternary stereocenters adjacent to a tertiary benzylic stereocenter and are formed with high levels of stereocontrol.
- Logan, Angus W.J.,Parker, Jeremy S.,Hallside, Michal S.,Burton, Jonathan W.
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supporting information; experimental part
p. 2940 - 2943
(2012/08/28)
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- A facile synthesis of α-fluoro ketones catalyzed by [Cp*IrCl2]2
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Allylic alcohols are isomerized into enolates (enols) by [Cp*IrCl2]2. The enolates react with Selectfluor present in the reaction media. This method produces α-fluoro ketones as single constitutional isomers in high yields. Georg Thieme Verlag Stuttgart. New York.
- Ahlsten, Nanna,Bartoszewicz, Agnieszka,Agrawal, Santosh,Martin-Matute, Belen
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supporting information; experimental part
p. 2600 - 2608
(2011/10/02)
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- 1-Alkyl-2,3-dihydro-4(1H)-quinolinones by a tandem Michael-SNAr annulation reaction
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(Chemical Equation Presented) A tandem Michael-SNAr annulation reaction has been developed for the synthesis of 1-alkyl-2,3-dihydro-4(1H)- quinolinones. Success in the reaction followed expected electronic effects for the final SNAr
- Bunce, Richard A.,Nago, Takahiro
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experimental part
p. 623 - 628
(2009/11/30)
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- Sequential catalytic isomerization and allylic substitution. Conversion of racemic branched allylic carbonates to enantioenriched allylic substitution products
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A catalytic protocol for the conversion of readily accessible racemic, branched aromatic allylic esters to branched allylic amines, ethers, and alkyls has been developed. Palladium-catalyzed isomerization of branched allylic esters to terminal allylic esters, followed by sequential iridium-catalyzed allylic substitution, gave the branched allylic products in good yield with high regioisomeric and enantiomeric selectivity. Both electron-rich and electron-poor branched allylic esters gave products in >90% ee. High enantiomeric excesses were also observed for the products from the reactions of 2-thienyl acetates and dienyl carbonates. Copyright
- Shekhar, Shashank,Trantow, Brian,Leitner, Andreas,Hartwig, John F.
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p. 11770 - 11771
(2007/10/03)
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