Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki–Miyaura cross-coupling

Hoang, Gia L.; Takacs, James M.

doi:10.1039/c7sc01093a

Cited by 46 publications

(19 citation statements)

References 101 publications

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“…Most recently, this scope has been extended to include a wide range of Csp 3 and Xsp 3 coupling partners, 118–120 including even stereospecific Csp 3 cross-couplings of stereochemically defined chiral non-racemic building blocks, originally pioneered by Crudden. 121–131 These new methods, combined with anticipated major additional advances in the area of sp 3 cross-coupling over the next few decades, suggest that iterative cross-coupling could represent a generalizable approach for building block-based small molecule synthesis.…”

Section: Advances Towards a General Platform For Iterative Small Molementioning

confidence: 99%

Towards the generalized iterative synthesis of small molecules

2018

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Small molecules have extensive untapped potential to benefit society, but access to this potential is too often restricted by limitations inherent to the customized approach currently used to synthesize this class of chemical matter. In contrast, the “building block approach”, i.e., generalized iterative assembly of interchangeable parts, has now proven to be a highly efficient and flexible way to construct things ranging all the way from skyscrapers to macromolecules to artificial intelligence algorithms. The structural redundancy found in many small molecules suggests that they possess a similar capacity for generalized building block-based construction. It is also encouraging that many customized iterative synthesis methods have been developed that improve access to specific classes of small molecules. There has also been substantial recent progress toward the iterative assembly of many different types of small molecules, including complex natural products, pharmaceuticals, biological probes, and materials, using common building blocks and coupling chemistry. Collectively, these advances suggest that a generalized building block approach for small molecule synthesis may be within reach.

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Section: Advances Towards a General Platform For Iterative Small Molementioning

confidence: 99%

Towards the generalized iterative synthesis of small molecules

2018

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“…For example, Rh‐ or Ir‐catalyzed hydroborations of alkenes with tethered directing groups proceeded in a substrate‐chelation mechanism because of the availability of multiple coordination sites on the metal center. The regioselectivity was governed through the coordination of directing groups such as amides and oximes to the transition‐metal center, selectively affording β‐borylated products in preference to γ‐isomers –. The proximal regioselectivity could also be controlled by inductive effects .…”

Section: Methodsmentioning

confidence: 99%

Iridium‐Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes

et al. 2019

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“…Minor amounts of the cis product diastereomer were also obtained. Their origin remains to be concretely identified, but we tentatively propose cis diastereomers may arise in the case of 7 owing to a weak coordinative directing effect exerted by the β‐amide substituent on the nickel catalyst that ultimately results in C(sp 3 )−C(sp 2 ) bond formation on the same side of the cyclobutane ring …”

Section: Methodsmentioning

confidence: 99%