Electrophile-induced 1,2-Metallate Rearrangement of Alkenyl Borates
نویسندگان
چکیده
منابع مشابه
Asymmetric lithiation-substitution of amines involving rearrangement of borates.
Asymmetric lithiation of substituted benzylamines, N-Boc-pyrrolidine, or N-Boc-indoline using Beak's methodology was followed by electrophilic quench with trialkylboranes. The resulting borate intermediates rearrange with concomitant C-N bond breakage to give, after oxidation, chiral secondary alcohols with high enantioselectivity.
متن کاملHomologation and alkylation of boronic esters and boranes by 1,2-metallate rearrangement of boronate complexes.
Organoboranes and boronic esters readily undergo nucleophilic addition, and if the nucleophile also bears an alpha-leaving group, 1,2-metallate rearrangement of the ate complex results. Through such a process a carbon chain can be extended, usually with high stereocontrol and this is the focus of this review. A chiral boronic ester (substrate control) can be used for stereocontrolled homologati...
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The 2-Aza-Cope rearrangement of γ-alkenyl nitrones is a rare example of the neutral thermal 2-aza-Cope process that usually takes place with cationic species. During the rearrangement, a redistribution of bonds and electronic density occurs in one kinetic step. However, the introduction of substituents with different steric requirements and electronic features might alter the activation energie...
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N-Alkyl 2-pyridones and other enolizable heterocycles are important synthetic constructs, due to their prevalence in natural products and pharmaceutical targets and their capacity to serve as models for a number of biological and chemical processes. The disclosed Au(I)-catalyzed reaction utilizes 2-propargyloxypyridines to access N-alkylated 2-pyridone products derived from both 5-exo and 6-end...
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New synthetic methods to rapidly access useful fluorophores are needed to advance modern molecular imaging techniques. A new variant of the classical Smiles rearrangement is reported that enables the efficient synthesis of previously inaccessible C4'-O-alkyl heptamethine cyanines. The key reaction involves N- to O-transposition with selective electrophile incorporation on nitrogen. A representa...
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ژورنال
عنوان ژورنال: Journal of Synthetic Organic Chemistry, Japan
سال: 2018
ISSN: 0037-9980,1883-6526
DOI: 10.5059/yukigoseikyokaishi.76.57