Stereocontrolled Synthesis of Cyclobutylamines Enabled by Lewis Acid-Catalyzed (3 + 2 + 2) Cycloaddition/Ring-Opening Strategy of Bicyclo[1.1.0]butanes with Triazinanes.
Sign Up to like & getrecommendations! Published in 2024 at "Organic letters"
DOI: 10.1021/acs.orglett.4c03862
Abstract: Herein, we develop a modular and efficient "cycloaddition/ring-opening" strategy of bicyclo[1.1.0]butanes (BCBs) with triazinanes to provide a series of syn-diastereoselective cyclobutylamines via 2,4-diazabicyclo[4.1.1]octanes (aza-BCOs). The reaction features simple operation, mild reaction conditions, and a broad… read more here.
Keywords: strategy bicyclo; ring opening; bicyclo butanes; opening strategy ... See more keywords
Photoinduced Cobaloxime-Catalyzed Regio- and Diastereoselective Hydrogen-Evolution C(sp3)-H Phosphorylation of Bicyclo[1.1.0]butanes.
Sign Up to like & getrecommendations! Published in 2025 at "Organic letters"
DOI: 10.1021/acs.orglett.4c04702
Abstract: Radical-initiated functionalization of bicyclo[1.1.0]butanes (BCBs) is a straightforward approach to accessing diverse cyclobutane derivatives. However, selective C(sp3)-H functionalization at the C2 position of BCBs remains scarce. Herein, a mild protocol for the hydrogen-evolution of C2… read more here.
Keywords: sp3; evolution sp3; sp3 phosphorylation; hydrogen evolution ... See more keywords
FeCl3-Catalyzed Intermolecular Formal [8π+2σ] Cycloaddition of Azaheptafulvene with Bicyclo[1.1.0]butanes for the Synthesis of Cycloheptatriene-Fused 2-Azabicyclo[3.1.1]heptanes.
Sign Up to like & getrecommendations! Published in 2025 at "Organic letters"
DOI: 10.1021/acs.orglett.5c00489
Abstract: Higher-order cycloadditions are a simple and effective strategy for constructing significant medium-sized architectures. Azaheptafulvenes reacting with readily accessible bicyclo[1.1.0]butanes (BCBs) through FeCl3-promoted intermolecular formal [8π+2σ] cycloaddition reactions to access cycloheptatriene-fused 2-azabicyclo[3.1.1]heptanes have been developed. This… read more here.
Keywords: fused azabicyclo; intermolecular formal; formal cycloaddition; azabicyclo heptanes ... See more keywords
Energy Transfer Mediated [2π + 2σ] Photocycloaddition of Bicyclo[1.1.0]butanes with Maleimides: Formation of Potential Bioisotere of Phthalimide.
Sign Up to like & getrecommendations! Published in 2025 at "Organic letters"
DOI: 10.1021/acs.orglett.5c01779
Abstract: Replacing aromatic rings with 3D sp3-rich cage structures is a promising strategy in medicinal chemistry for improving the physicochemical and pharmacokinetic profiles of drug candidates. This manuscript disclosed the [2π + 2σ] cycloaddition maleimides with… read more here.
Keywords: phthalimide; energy transfer; bicyclo butanes; transfer mediated ... See more keywords
HFIP-Mediated Spiro-annulation of Bicyclo[1.1.0]butanes with α-Halo Hydroxamates: Access to Functionalized Spirocyclobutenes.
Sign Up to like & getrecommendations! Published in 2025 at "Organic letters"
DOI: 10.1021/acs.orglett.5c02493
Abstract: Bicyclo[1.1.0]butanes (BCBs) are activated using photocatalysts, Lewis and Brønsted acids, transition metal catalysts, and more recently hexafluoroisopropanol (HFIP). On the other hand, α-halo hydroxamates are known to generate reactive azaoxyallyl cations in the presence of… read more here.
Keywords: spiro annulation; functionalized spirocyclobutenes; halo hydroxamates; bicyclo butanes ... See more keywords
HFIP-Mediated Ring Opening of Bicyclo[1.1.0]butanes with Hydroperoxides for Diastereoselective Access to Peroxycyclobutanes.
Sign Up to like & getrecommendations! Published in 2025 at "Organic letters"
DOI: 10.1021/acs.orglett.5c03346
Abstract: A transition-metal-free ring opening of bicyclo[1.1.0]butanes (BCBs) using hydroperoxides as nucleophiles in hexafluoroisopropanol (HFIP) resulting in the diastereoselective synthesis of peroxycyclobutanes under mild conditions with a broad scope is demonstrated. Preliminary mechanistic experiments, including density… read more here.
Keywords: ring opening; mediated ring; opening bicyclo; hfip mediated ... See more keywords
Synthesis of Azabicyclo[3.1.1]heptenes Enabled by Catalyst-Controlled Annulations of Bicyclo[1.1.0]butanes with Vinyl Azides.
Sign Up to like & getrecommendations! Published in 2024 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.4c04485
Abstract: Bridged bicyclic scaffolds are emerging bioisosteres of planar aromatic rings under the concept of "escape from flatland". However, adopting this concept into the exploration of bioisosteres of pyridines remains elusive due to the challenge of… read more here.
Keywords: synthesis azabicyclo; vinyl azides; azabicyclo heptenes; bioisosteres pyridines ... See more keywords
Catalytic Intermolecular Asymmetric [2π + 2σ] Cycloadditions of Bicyclo[1.1.0]butanes: Practical Synthesis of Enantioenriched Highly Substituted Bicyclo[2.1.1]hexanes.
Sign Up to like & getrecommendations! Published in 2024 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.4c10968
Abstract: The high percentage of sp3-hybridized carbons and the presence of chiral carbon centers could contribute to increased molecular complexity, enhancing the likelihood of clinical success of drug candidates. Three-dimensional (3D) bridged motifs have recently garnered… read more here.
Keywords: bicyclo; highly substituted; bicyclo butanes; intermolecular asymmetric ... See more keywords
Enantioselective Synthesis of Tetrahydro-1H-1,3-methanocarbazoles by Formal (3 + 3)-Cycloaddition Using Bicyclo[1.1.0]butanes.
Sign Up to like & getrecommendations! Published in 2025 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.4c14276
Abstract: Asymmetric synthesis presents many challenges, with the selective formation of chiral bridged polyheterocycles being a notable example. Cycloadditions using bicyclo[1.1.0]butanes (BCB) offer a promising solution along those lines, yet, despite significant advances in that emerging… read more here.
Keywords: formal cycloaddition; tetrahydro; synthesis; bicyclo butanes ... See more keywords
Asymmetric Dearomative [2 + 2] Photocycloaddition of Quinoline and Indole Derivatives with Bicyclo[1.1.0]butanes.
Sign Up to like & getrecommendations! Published in 2025 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.5c12057
Abstract: The dearomative photocycloaddition reactions of (hetero)arene feedstocks have emerged as an efficient platform for the construction of three-dimensional complexity, which is of increasing interest in medicinal chemistry. Nevertheless, the catalytic asymmetric version of such transformations… read more here.
Keywords: dearomative photocycloaddition; asymmetric dearomative; bicyclo butanes; regio diastereo ... See more keywords
Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Bicyclo[1.1.0]butanes.
Sign Up to like & getrecommendations! Published in 2025 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.5c16702
Abstract: Bicyclo[1.1.0]butanes (BCBs) have attracted considerable interest in organic synthesis due to their versatile reactivity. However, the asymmetric synthesis of these strained systems remains a formidable challenge. We herein report an iridium-catalyzed enantioselective C(sp3)-H borylation of… read more here.
Keywords: catalyzed enantioselective; iridium catalyzed; sp3 borylation; bicyclo butanes ... See more keywords