Convergent, asymmetric synthesis of vicinal amino alcohols via Rh-catalyzed addition of α-amido trifluoroborates to carbonyls

Abstract

The convergent, asymmetric synthesis of vicinal amino alcohols is achieved by the Rh-catalyzed addition of α-amido trifluoroborates to carbonyl compounds.

Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles

“… 3 In addition, their use in transition-metal-catalyzed stereospecific C–C bond forming reactions has also gained growing attention. 4 Therefore, significant efforts have been devoted to the development of efficient methods to synthesize chiral α-amino boronate esters. 5 Most methods rely on a diastereoselective synthesis involving a stoichiometric amount of chiral auxiliaries.…”

Synthesis of Chiral Tertiary Boronic Esters by Oxime‐Directed Catalytic Asymmetric Hydroboration

“…[7] In particular, recent reviews by Aggarwal highlight transformations of chiral tertiary boronic esters, [ 8 ] including their use for the construction of multiple contiguous quaternary stereocenters. [9] However, the formation of tertiary organoboronates via metal-catalyzed or stoichiometric hydroboration, is rare since hydroboration generally proceeds in an anti-Markovnikov fashion delivering boron to the less substituted site on the alkene.…”

Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki–Miyaura Cross-Coupling

“…As first demonstrated by Crudden, 1g,2 Suzuki-Miyaura cross-couplings of α-chiral alkylboron compounds possessing adjacent π-systems proceed with stereoretention. However, substrates similar to those used here by Molander 22 and Suginome, 23 as well as other substrates reported by Biscoe, 1a Morken 4b and Hall, 24 proceed with stereoinversion. For example, the borylated amides 17 and 19 undergo palladium-catalyzed cross-coupling with near complete stereoinversion (Figure 5).…”

“…Chiral organoboronates are useful intermediates in organic synthesis, 1,2 and consequently, a number of research groups are developing enantioselective methods for their preparation. 3–10 We reported the rhodium-catalyzed carbonyl-directed catalytic asymmetric hydroborations (directed CAHBs) of certain ( E)- and (Z)- disubstituted and -trisubstituted β,γ-unsaturated amides 1 and 1,1-disubstituted (i.e., methylidene) β,γ-unsaturated amides and tert- butyl esters 3 .…”