Gram Scale Conversion of <i>R</i>-BINAM to <i>R</i>-NOBIN

Patel, Darshan C.; Breitbach, Zachary S.; Woods, Ross M.; Lim, Yeeun; Andy, Wang; Foss, Frank W.; Armstrong, Daniel W.

doi:10.1021/acs.joc.5b02663

Cited by 34 publications

(9 citation statements)

References 54 publications

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“…Though the racemic NOBIN was firstly reported early in 1991, optically pure NOBINs are mainly obtained by using the transformation from other chiral binaphthyls, [8a,b] the chiral substrate induction [8c] and the indirect asymmetric catalyzed methods requiring protecting groups on the substrates. Maruoka and Zhao synthesized enantioenriched NOBINs by kinetic resolution requiring the NH 2 and/or OH group to be protected (Scheme 1 b).…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Synthesis of 3,3′‐Disubstituted 2‐Amino‐2′‐hydroxy‐1,1′‐binaphthyls by Copper‐Catalyzed Aerobic Oxidative Cross‐Coupling

Zhao

Ding

et al. 2021

Angewandte Chemie

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A challenging direct asymmetric catalytic aerobic oxidative cross‐coupling of 2‐naphthylamine and 2‐naphthol, using a novel CuI/SPDO system, has been successfully developed for the first time. Enantioenriched 3,3′‐disubstituted NOBINs were achieved and could be readily derived to divergent chiral ligands and catalysts. This reaction features high enantioselectivities (up to 96 % ee) and good yields (up to 80 %). The DFT calculations suggest that the F–H interactions between CF3 of L17 and H‐1,8 of 2‐naphthol, and the π–π stacking between the two coupling partners could play vital roles in the enantiocontrol of this cross‐coupling reaction.

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Section: Methodsmentioning

confidence: 99%

Enantioselective Synthesis of 3,3′‐Disubstituted 2‐Amino‐2′‐hydroxy‐1,1′‐binaphthyls by Copper‐Catalyzed Aerobic Oxidative Cross‐Coupling

Zhao

Ding

et al. 2021

Angewandte Chemie

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“…For NOBIN and its derivatives, they could be accessed from other binaphthyl compounds such as BINOL or BINAM [ 14 , 15 , 16 ]. However, in these synthetic processes, excess noble metal reagents, harsh conditions, or expensive reagents were commonly required to achieve satisfactory efficiency [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed Synthesis of Axially Chiral Biaryls with Diaryliodonium Salts as Arylation Reagents

Zhang

Xiang

et al. 2021

Molecules

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NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation of N-arylhydroxylamines or N-arylhydrazines with diaryliodonium salts and [3,3]-sigmatropic rearrangement. This reaction features mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols.

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“…Shortly after, optical resolution rapidly developed into the next attractive method to isolate NOBIN enantiomers by leveraging the power of diastereoisomeric chiral salt formation, but was confined to unstable reproducibility in practical 26,27 . Getting the NOBIN derivatives through a direct transformation from chiral raw materials (e.g., BINOL 28 or BINAM 29 ) has also become an interesting way. Regrettably, this protocol is mostly applied to construct chiral binaphthyl-type amino-alcohols.…”

Section: Introductionmentioning

confidence: 99%

NHC-catalyzed atropoenantioselective synthesis of axially chiral biaryl amino alcohols via a cooperative strategy

et al. 2019

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Axially chiral biaryl amino-alcohols play a pivotal role in organic synthesis and drug discovery. However, only a very few enantioselective methods have been reported to synthesize chiral biaryl amino-alcohols. Therefore, the rapid enantioselective construction of optically active biaryl amino-alcohols still remains a formidable challenge. Here we report an N-heterocyclic carbene (NHC)-catalyzed atropoenantioselective acylation of biphenols triggered by a cooperative strategy consisting of desymmetrization followed by kinetic resolution. This protocol features broad substrate scope and good functional group tolerance, and allows for a rapid construction of axially chiral biaryl amino-alcohols in good to high yields and with excellent enantioselectivities. Furthermore, the structurally diverse axially chiral biaryl amino-alcohol derivatives provide multiple possibilities for chemists to develop catalysts or ligands for different chemical transformations.

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Gram Scale Conversion of R-BINAM to R-NOBIN

Cited by 34 publications

References 54 publications

Enantioselective Synthesis of 3,3′‐Disubstituted 2‐Amino‐2′‐hydroxy‐1,1′‐binaphthyls by Copper‐Catalyzed Aerobic Oxidative Cross‐Coupling

Enantioselective Synthesis of 3,3′‐Disubstituted 2‐Amino‐2′‐hydroxy‐1,1′‐binaphthyls by Copper‐Catalyzed Aerobic Oxidative Cross‐Coupling

Copper-Catalyzed Synthesis of Axially Chiral Biaryls with Diaryliodonium Salts as Arylation Reagents

NHC-catalyzed atropoenantioselective synthesis of axially chiral biaryl amino alcohols via a cooperative strategy

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