Asymmetric Catalysis with a Phosphoramidite Derived from (−)-(aR)- [1,1′-Binaphthalene]-8,8′-diol

Müller, Paul; Nury, Patrice; Bérnardinelli, Gerald

doi:10.1002/(sici)1522-2675(20000412)83:4<843::aid-hlca843>3.0.co;2-j

Cited by 22 publications

(9 citation statements)

References 15 publications

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“…The amidophosphates are known to be efficient inhibitors of various enzymes [1][2][3][4], they are used in the treatment of virus diseases [5], but the most practically interesting is the AIDS treatment [6] employing this class of organophosphorus compounds. Sometimes the amidophosphates are used as ionic polymerization initiators [7], in other events they are successfully applied as catalysts in asymmetric synthesis [8].…”

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confidence: 99%

Synthesis of new amidophosphates containing an adamantyl fragment under microwave irradiation

et al. 2010

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confidence: 99%

Synthesis of new amidophosphates containing an adamantyl fragment under microwave irradiation

et al. 2010

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“…Thus, this catalyst represents the most selective one for both cyclic and acyclic enones known to date. Very recently, a similar but less selective quinoline based ligand system was reported by Faraone and co-workers 23 whereas Müller et al 24 used a phosphorus amidite derived from 1,1'-binaphthalene-8,8'-diol.…”

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confidence: 83%

Recent Advances in Catalytic Enantioselective Michael Additions

Krause¹,

2001

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This review summarizes the tremendous achievements in the field of catalytic enantioselective Michael additions over the last few years. An impressive number of efficient catalytic systems has been established which are complementary to each other with respect to applicable Michael acceptors and donors. Copper phosphorus amidites, phosphites and phosphonates are the catalysts of choice for the highly enantioselective transfer of (functionalized or unfunctionalized) alkyl groups to cyclic and linear enones. For the corresponding arylations and alkenylations, however, Rhodium-BI-NAP catalysts are superior. Remarkably, efficient catalytic systems for Michael additions of malonates and other soft nucleophiles include copper(II) bisoxazolines and heterobimetal complexes. Very recently, even metal-free catalysts (e.g., alkaloids and peptides) are gaining importance for enantioselective Michael additions. Several applications of these catalysts in natural product syntheses document the high standard now reached in this field. 7 Other Catalytic Enantioselective Michael Additions 8 Conclusion

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“…In the presence of 2-10 mol% catalysts 5a,b, o-chloroacetophenone was reduced by BH 3 SMe 2 with 35-46% ee [12]. Similarly, 5 mol% 10b gave almost quantitative yield and 96% ee [19]. Similarly, 5 mol% 10b gave almost quantitative yield and 96% ee [19].…”

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confidence: 96%

Reduction of Carbonyl Compounds

Berkessel

Gröger

2005

Asymmetric Organocatalysis

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Organocatalytic asymmetric carbonyl reductions have been achieved with boranes in the presence of oxazaborolidine and phosphorus-based catalysts (Section 11.1), with borohydride reagents in the presence of phase-transfer catalysts (Section 11.2), and with hydrosilanes in the presence of chiral nucleophilic activators (Section 11.3). Borane Reduction Catalyzed by Oxazaborolidines and Phosphorus-based CatalystsProbably the most frequently applied catalytic metal-free and highly enantioselective reduction of carbonyl compounds is the oxazaborolidine-catalyzed borane reduction (the Corey-Bakshi-Shibata (CBS) method) [1][2][3][4][5][6][7][8]. In this approach, which is based on initial work by Itsuno et al. [1,[6][7][8], oxazaborolidines serve as the catalysts. These latter materials are derived from readily available amino alcohols; the most frequently used is probably the proline-derived bicyclic compound 4. The CBS method has been successfully applied to all types of ketones, for example diaryl, dialkyl, and aryl alkyl ketones, haloalkyl ketones, transition metal p-complexes of aryl alkyl ketones, cyclic and open-chain enones, etc. [1][2][3][4][5][6][7][8]. Scheme 11.1 shows the explicit example of acetophenone (1) which can be reduced with boranes such as BH 3 THF (2a), BH 3 Me 2 S, catechol borane, or the borane-diethylaniline complex (2b) to give 1-phenylethanol 3 in very good yields and almost perfect enantiomeric excess.Scheme 11.1 also summarizes other impressive examples of the performance of the CBS method [1][2][3][4][5][6][7][8]. Several excellent reviews on the CBS method have appeared recently [1, 2], and no detailed discussion of the development of the process or substrate scope shall be presented in this review. Please note, however, that the oxazaborolidine-catalyzed borane reduction of ketones is a prime example of bifunctional catalysis [2,9] -as shown in Scheme 11.2, the current mechanistic picture involves simultaneous binding of both the ketone and the borane to the Lewis-acidic (boron) and Lewis-basic (nitrogen) sites of the catalyst A. In the resulting ternary complex B, the reaction partners are synergistically activated toward hydride transfer.

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Asymmetric Catalysis with a Phosphoramidite Derived from (−)-(aR)- [1,1′-Binaphthalene]-8,8′-diol

Cited by 22 publications

References 15 publications

Synthesis of new amidophosphates containing an adamantyl fragment under microwave irradiation

Synthesis of new amidophosphates containing an adamantyl fragment under microwave irradiation

Recent Advances in Catalytic Enantioselective Michael Additions

Reduction of Carbonyl Compounds

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