- A Sequential Pd-AAA/Cross-Metathesis/Cope Rearrangement Strategy for the Stereoselective Synthesis of Chiral Butenolides
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A practical and highly enantio- (up to 94:6 er) and diastereoselective (up to >20:1 dr) synthesis of I-butenolides bearing two adjacent stereogenic centers is reported featuring a sequential direct palladium-catalyzed asymmetric allylic alkylation/(E)-selective cross-metathesis/[3,3]-sigmatropic Cope rearrangement from readily available α-substituted (5H)-furan-2-ones.
- Aubert, Sidonie,Katsina, Tania,Arseniyadis, Stellios
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p. 2231 - 2235
(2019/03/29)
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- Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide
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A Rh(III)-catalyzed C-H activation of boronic acid with aryl azide to obtain unsymmetric carbazoles, 1H-indoles, or indolines has been developed. The reaction constructs dual distinct C-N bonds via sp2/sp3 C-H activation and rhodium nitrene insertion. Synthetically, this approach represents an access to widely used carbazole derivatives. The practical application to CBP and unsymmetric TCTA derivatives has also been performed. Mechanistic experiments and DFT calculations demonstrate that a five-membered rhodacycle species is the key intermediate.
- Xu, Shiyang,Huang, Baoliang,Qiao, Guanyu,Huang, Ziyue,Zhang, Zhen,Li, Zongyang,Wang, Peng,Zhang, Zhenhua
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supporting information
p. 5578 - 5582
(2018/09/25)
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- Stereoselective Synthesis of Exocyclic Tetrasubstituted Vinyl Halides via Ru-Catalyzed Halotropic Cycloisomerization of 1,6-Haloenynes
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Herein, a ruthenium-catalyzed cycloisomerization that transforms 1,6-haloenynes into 5-membered carbo- and heterocycles that bear exocyclic, stereodefined, tetrasubstituted vinyl halides is reported. The reaction is insensitive to air and water, tolerates a variety of functional groups, and proceeds with good to excellent stereoselectivity and yield.
- Trost, Barry M.,Kalnmals, Christopher A.
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supporting information
p. 2346 - 2349
(2017/05/12)
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- Synthesis of substituted benzooxaborinin-1-ols via palladium-catalysed cyclisation of alkenyl- and alkynyl-boronic acids
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Two new palladium-catalysed reactions have been developed for the synthesis of stable 4-substituted benzooxaborinin-1-ols. A palladium-catalysed cyclisation of ortho-alkenylbenzene boronic acids can be used to access 4-chlorobenzooxaborinin-1-ols via a Wa
- Benhamou, Laure,Walker, Daniel W.,Bu?ar, Dejan-Kre?imir,Aliev, Abil E.,Sheppard, Tom D.
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supporting information
p. 8039 - 8043
(2016/09/09)
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- Bromo-boronolactonization of olefins
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Exposure of a variety of mono- and disubstituted ortho-alkenylarylboronic acids to NBS in THF/H2O under neutral conditions affords bromo-boronolactones, in some instances, with exceptional regiocontrol. The adducts, analogous to those formed by carboxylic acids, are shown to be useful synthetic intermediates.
- Falck,Bondlela,Venkataraman,Srinivas
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p. 7148 - 7150
(2007/10/03)
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