Enantio‐ and Diastereoselective Cyclopropanation of 1‐Alkenylboronates: Synthesis of 1‐Boryl‐2,3‐Disubstituted Cyclopropanes

Carreras, Javier; Caballero, Ana; Pérez, Pedro J.

doi:10.1002/anie.201710415

Cited by 51 publications

(34 citation statements)

References 74 publications

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“…[104] Moreover, we have recently described the first highly enantioand diastereoselectivec yclopropanation of 1-alkenyl boronates with ethyl diazoacetate by using Cu I -BOX complex as catalyst (Scheme 23b). [105] Epoxidation reactions have been studied under Sharpless conditions or using vanadium oxides for alkenyl boronates, [106] or with four-coordinated boron derivatives (ÀBF 3 K, ÀBMIDA, À BPIDA)i nt he presence of other commone poxidation reagents such as meta-chloroperoxybenzoic acid( m-CPBA) or DMDO (Scheme24). [107] In both cases, satisfying diastereoisomeric ratios have been obtained when using chiral auxiliaries (chiral Scheme21.…”

Section: Applications Of Alkenyl Boronatesmentioning

confidence: 99%

Alkenyl Boronates: Synthesis and Applications

Carreras

Caballero

Pérez

2019

Chemistry An Asian Journal

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180

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DedicatedtoProf. GregorioA sensio on the occasion of his 70th birthdayAbstract: Organoboron compounds have become one of the most versatile buildingb locks in organic synthesis owing to their accessible and efficient conversion into many different functional groups.I np articular,a lkenyl boronates have received ag reat deal of attentiona sv ery reactive substrates in Suzuki-Miyaura cross-coupling reactions. Accord-ingly,e fforts towards the development of efficient methods to prepare this type of compound are ongoing. In this contribution, the progress in the search for synthetic routes for alkenylb oronates and their use in av ariety of organic transformationsisa ccounted.

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Section: Applications Of Alkenyl Boronatesmentioning

confidence: 99%

Alkenyl Boronates: Synthesis and Applications

Carreras

Caballero

Pérez

2019

Chemistry An Asian Journal

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180

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“…Importantly, many interesting functionalized carbenes ( 6 – 12 ; FG‐

\overset{. .}{normalC}

‐H), such as alkyl‐,, hydroxy‐, amino‐, boryl‐, selenyl‐, heteroaryl‐, or alkenyl‐methylidenes are too unstable to engage in cyclopropanation reactions. As a result, the derived cyclopropanes still require long and specific syntheses ,…”

Section: Methodsmentioning

confidence: 99%

General Cyclopropane Assembly by Enantioselective Transfer of a Redox‐Active Carbene to Aliphatic Olefins

et al. 2019

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Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates, and reagents, even when targeting similar compounds. This approach slows down discovery and limits available chemical space. Introduced herein is a practical and versatile diazocompound and its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. The redox‐active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect allowed the asymmetric cyclopropanation of various olefins, including unfunctionalized aliphatic alkenes, that enables the three‐step total synthesis of (−)‐dictyopterene A. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally differentiated diazocompounds are viable and advantageous equivalents of single‐carbon chirons.

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“…22 In 2018, Perez and co-workers reported an enantioselective copper-catalyzed version of this transformation in the case of ethyl diazoacetate (Scheme 20). 51 The method relied on the use of Evans chiral ligand 50, and 1,2,3-trisubstituted cyclopropanes 51 were obtained in good yields (56-86%) with high diastereo-(dr 94:6 to 97:3) and enantioselectivi-ty (er 94:6 to 99:1). The methodology exhibited good tolerance to different substitution patterns at the aromatic ring of starting boronate 52 (R = aryl).…”

Section: Scheme 19 Cyclopropanation Of Alkenyl Boronate 21 With Simmomentioning

confidence: 99%

Cycloadditions of Alkenylboronic Derivatives

et al. 2020

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The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addressed less thoroughly in the previous works.1 Introduction2 [2+1] Cycloaddition2.1 Cyclopropanation2.1.1 With Methylene Synthetic Equivalents2.1.2 With Substituted Carbenoids2.2 Epoxidation2.3 Aziridination3 [2+2] Cycloaddition4 [3+2] Cycloaddition4.1 With Nitrile Oxides4.2 With Diazoalkanes4.3 With Nitrones4.4 With Azomethine Ylides5 [4+2] Cycloaddition6 [4+3] Cycloaddition7 Conclusions and Outlook

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Enantio‐ and Diastereoselective Cyclopropanation of 1‐Alkenylboronates: Synthesis of 1‐Boryl‐2,3‐Disubstituted Cyclopropanes

Cited by 51 publications

References 74 publications

Alkenyl Boronates: Synthesis and Applications

Alkenyl Boronates: Synthesis and Applications

General Cyclopropane Assembly by Enantioselective Transfer of a Redox‐Active Carbene to Aliphatic Olefins

Cycloadditions of Alkenylboronic Derivatives

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