Journal ArticleDOI
Asymmetric Conjugate Addition of Alkynylboronates to Enones: Rationale for the Intriguing Catalysis Exerted by Binaphthols
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The conjugate addition of alkynylboronates to enones catalyzed by binaphthols has been studied theoretically with DFT methods and the competing hetero-Diels-Alder reactions are computed to be kinetically disfavored relative to alkynyborations.Abstract:
The conjugate addition of alkynylboronates to enones catalyzed by binaphthols has been studied theoretically with DFT methods. The high reactivity of the alkynylboronate derived from binaphthol seems to arise from electronic effects since its acidic boron atom binds tightly to the enone carbonyl and lowers the activation energy of the alkynylboration step. Steric clashes between the atoms of the ligands on boron and the enone can be invoked to account for the observed facial diastereoselectivity. The competing hetero-Diels−Alder reactions are computed to be kinetically disfavored relative to alkynylborations.read more
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Book ChapterDOI
Structure, Properties, and Preparation of Boronic Acid Derivatives. Overview of Their Reactions and Applications
TL;DR: Boronic acids as mentioned in this paper are trivalent boron-containing organic compounds that possess one alkyl substituent (i.e., a C-B bond) and two hydroxyl groups.
Journal ArticleDOI
Transition-metal-free C-C bond forming reactions of aryl, alkenyl and alkynylboronic acids and their derivatives.
Silvia Roscales,Aurelio G. Csaky +1 more
TL;DR: In this tutorial review, some new methods for C-C bond formation using aryl-, alkenyl- and alkynylboronic acids under transition-metal-free conditions are beginning to emerge.
Journal ArticleDOI
Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes.
TL;DR: Mechanistic experiments suggest the intermediacy of 1,2-bonded diboronates, and catalytic enantioselective diboration of alkenes is accomplished with readily available carbohydrate-derived catalysts.
Journal ArticleDOI
Aerobic Alcohol Oxidation Coupled to Palladium-Catalyzed Alkene Hydroarylation with Boronic Esters†
TL;DR: The Suzuki reaction, which couples an organohalide and an organoboron compound, is an attractive cross-coupling reaction for use in the synthesis of natural products and pharmaceuticals because of the excellent functional group compatibility, ease of preparation of boronic acid derivatives, and the low toxicity of the boron byproducts.
References
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Journal ArticleDOI
Generation and use of a zinc derivative of a functionalized 1,3-oxazole. Solution of the virginiamycin/madumycin oxazole problem
TL;DR: In this paper, a new heteroaromatic ''benzylic'' organozinc derivative which undergoes nucleophic addition to a variety of aldehydes and ketones is envisioned; application to the synthesis of virginiamycin and other streptogramin antibiotics is envisioned
Journal ArticleDOI
Reaction of 1,3-dimethyl-5-acetyl-barbituric acid (DAB) with primary amines. Access to intermediates for selectively protected spermidines
TL;DR: The ability of 1,3-dimethyl-5-acetyl-barbituric acid (DAB) to react with primary amines in a chemoselective fashion was applied to the synthesis of a selectively protected spermidine as mentioned in this paper.
Journal ArticleDOI
A DFT study on the regioselectivity of the reaction of dichloropropynylborane with isoprene.
TL;DR: The " meta" regioselectivity observed experimentally for the reaction between 2-substituted 1,3-dienes and alkynyldihaloboranes has been explained as a result of the higher stabilization of these transition structures with "meta" orientation.
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