A convenient protocol for the synthesis of axially chiral Brønsted acids

Bartoszek, M.; Beller, Matthias; Deutsch, J.; Klawonn, Markus; Köckritz, Angela; Nemati, Navid; Pews‐Davtyan, Anahit

doi:10.1016/j.tet.2007.11.067

Cited by 60 publications

(32 citation statements)

References 53 publications

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“…On the other hand, they possess a wider substrate scope than enzymes and can be used in a variety of organic solvents. [26][27][28][29][30][31][32][33][34] It is further well known that incorporation of fluorine into an organic moiety markedly influences the bioactivity of the molecule. 35 In our previous work, we designed and synthesized a series of a-aminophosphonates containing a fluorine moiety.…”

Section: Introductionmentioning

confidence: 99%

An effective route to fluorine containing asymmetric α‐aminophosphonates using chiral Bronsted acid catalyst

Bhadury

Zhang

et al. 2008

Chirality

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Asymmetric addition of dialkyl phosphites (--CH2CH3, --CH2CH2CH3, --CH(CH3)2, --CH2(CH2)3CH3, --CH2CH2OCH3 and --CH2CH2OC2H5) induced by chiral organocatalyst e.g. (R)- and (S)-3,3'-[3,5-bis(trifluoromethyl)phenyl]2-1,1'-binaphthyl phosphate on fluorinated aldimines derived from cinnamaldehyde has been found effective to give new bioactive alpha-aminophosphonates in good yields (58-73%) and high enantiomeric excess (64.6%-90.6%) under mild conditions.

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Section: Introductionmentioning

confidence: 99%

An effective route to fluorine containing asymmetric α‐aminophosphonates using chiral Bronsted acid catalyst

Bhadury

Zhang

et al. 2008

Chirality

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“…[20] Having a similar aim of devising a synthesis of chiral BNP without the use of protecting groups, Bartoszek et al recently reported the direct Suzuki coupling of 3,3Ј-dibromo-H8-BINOL, which was followed by esterification with phosphoryl chloride to yield the substituted BNPH. [21] This Suzuki coupling of the BINOLs was successfully carried out at ambient temperature using Pd(OAc) 2 and Beller's ligand, PAd 2 Bu. [22] Under our present conditions, although the Suzuki coupling of BINOL 3a with an alkylboronic acid proceeded, the reaction was more sluggish, and much monosubstituted product 17a was obtained (Table 4, Entry 1).…”

Section: Resultsmentioning

confidence: 99%

A Protecting‐Group‐Free Route to Chiral BINOL–Phosphoric Acids

Chiu

2011

Eur J Org Chem

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A two‐step, protecting group‐free route for the synthesis of 3,3′‐disubstituted and 6,6′‐disubstituted chiral BINOL–phosphoric acids has been realized starting from commercially available brominated BINOLs. This synthesis relies on the direct Suzuki coupling of brominated BINOL phosphoric acids. This synthetic strategy is more efficient compared to previous circuitous strategies involving protections and deprotections, and the process is higher yielding relative to the alternative two‐step synthesis involving Suzuki coupling of the BINOL.

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“…8 One key feature of the methodology is the use of the bulky and electron-rich n-butyl-di-1-adamantylphosphine 4 to generate biaryl products with high yields (Fig. 2).…”

Section: Resultsmentioning

confidence: 99%