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3 article(s) from Wang, An

Organocatalyzed enantioselective desymmetrization of aziridines and epoxides

Ping-An Wang

Beilstein J. Org. Chem. 2013, 9, 1677–1695, doi:10.3762/bjoc.9.192

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Graphical Abstract

Figure 1: The catalyzed enantioselective desymmetrization.

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Figure 2: Cinchona alkaloid-derived catalysts OC-1 to OC-11.

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Scheme 1: The enantioselective desymmetrization of meso-aziridines in the presence of selected Cinchona alkal...

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Figure 3: Cinchona alkaloid-derived catalysts OC-12 to OC-19.

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Scheme 2: The enantioselective ring-opening of aziridines in the presence of OC-16.

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Scheme 3: OC-16 catalyzed enantioselective ring-opening of aziridines.

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Figure 4: The chiral phosphoric acids catalysts OC-20 and OC-21.

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Scheme 4: OC-20 and OC-21 catalyzed enantioselective desymmetrization of meso-aziridines.

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Figure 5: The proposed mechanism for chiral phosphorous acid-induced enantioselctive desymmetrization of meso...

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Scheme 5: OC-21 catalyzed enantioselective desymmetrization of meso-aziridines by Me₃SiSPh.

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Scheme 6: OC-21 catalyzed the enantioselective desymmetrization of meso-aziridines by Me₃SiSePh/PhSeH.

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Figure 6: L-Proline and its derivatives OC-22 to OC-27.

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Scheme 7: OC-23 catalyzed enantioselective desymmetrization of meso-aziridines.

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Figure 7: Proposed bifunctional mode of action of OC-23.

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Figure 8: The chiral thioureas OC-28 to OC-44 for the desymmetrization of meso-aziridines.

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Scheme 8: Desymmetrization of meso-aziridines with OC-41.

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Figure 9: The chiral guanidines (OC-45 to OC-48).

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Scheme 9: OC-46 catalyzed desymmetrization of meso-aziridines by arylthiols.

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Scheme 10: Desymmetrization of cis-aziridine-2,3-dicarboxylate.

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Figure 10: The proposed activation mode of OC-46.

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Scheme 11: The enantioselective desymmetrization of meso-aziridines by amine/CS₂ in the presence of OC-46.

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Figure 11: The chiral 1,2,3-triazolium chlorides OC-49 to OC-55.

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Scheme 12: The enantioselective desymmetrization of meso-aziridines by Me₃SiX (X = Cl or Br) in the presence o...

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Figure 12: Early organocatalysts for enantioselective desymmetrization of meso-epoxides.

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Scheme 13: Attempts of enantioselective desymmetrization of meso-epoxides in the presence of OC-58 or OC-60.

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Scheme 14: The enantioselective desymmetrization of a meso-epoxide containing one P atom.

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Figure 13: Some chiral phosphoramide and chiral phosphine oxides.

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Scheme 15: OC-62 catalyzed enantioselective desymmetrization of meso-epoxides by SiCl₄.

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Figure 14: The proposed mechanism of the chiral HMPA-catalyzed desymmetrization of meso-epoxides.

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Scheme 16: The enantioselective desymmetrization of meso-epoxides in the presence of OC-63.

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Figure 15: The Chiral phosphine oxides (OC-70 to OC-77) based on an allene backbone.

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Scheme 17: OC-73 catalyzed enantioselective desymmetrization of meso-epoxides by SiCl₄.

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Figure 16: Chiral pyridine N-oxides used in enantioselective desymmetrization of meso-epoxides.

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Scheme 18: Catalyzed enantioselective desymmetrization of meso-epoxides in the presence of OC-80 or OC-82.

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Figure 17: Chiral pyridine N-oxides OC-85 to OC-94.

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Scheme 19: Enantioselective desymmetrization of cis-stilbene oxide by using OC-85 to OC-92 as catalysts.

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Figure 18: A novel family of helical chiral pyridine N-oxides OC-95 to OC-97.

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Scheme 20: Desymmetrization of meso-epoxides catalyzed by OC-95 to OC-97.

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Scheme 21: OC-98 catalyzed enantioselective desymmetrization of meso-epoxides by SiCl₄.

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Review

Published 15 Aug 2013

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One-pot tandem cyclization of enantiopure asymmetric cis-2,5-disubstituted pyrrolidines: Facile access to chiral 10-heteroazatriquinanes

Ping-An Wang,
Sheng-Yong Zhang and
Henri B. Kagan

Beilstein J. Org. Chem. 2013, 9, 265–269, doi:10.3762/bjoc.9.32

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Graphical Abstract

Figure 1: The structures of azatriquinanes and azatriquinacene.

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Figure 2: The synthesis of 4 (previous work).

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Scheme 1: The designed synthetic route to a hydroxy NHC from 4b.

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Scheme 2: The reduction of amides 4 by LiAlH₄ and BH₃·THF.

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Figure 3: X-ray crystal structure of compound 5a.

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Scheme 3: One-pot tandem cyclization of 6 in the presence of HC(OCH₃)₃.

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Figure 4: X-ray crystal structure of compound 7b.

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Figure 5: The structural comparison of chiral ammonium salts such as 7 with the chiral PTCs of Denmark et al.

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Published 07 Feb 2013

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Convergent syntheses of Le^X analogues

An Wang,
Jenifer Hendel and
France-Isabelle Auzanneau

Beilstein J. Org. Chem. 2010, 6, No. 17, doi:10.3762/bjoc.6.17

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Graphical Abstract

Figure 1: Structure of Le^x analogues 1–3.

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Figure 2: Monosaccharide glycosyl acceptors (4–6) and donors (7–9) used in this study.

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Scheme 1: Synthesis of monosaccharide glycosyl acceptors 4–6.

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Scheme 2: Synthesis of the galactosyl donor 8.

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Scheme 3: Convergent synthesis of trisaccharides 29–32.

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Scheme 4: Proposed mechanism for the desulfurization of thioacetate 31 under dissolving metal conditions.

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Published 22 Feb 2010

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Organocatalyzed enantioselective desymmetrization of aziridines and epoxides

One-pot tandem cyclization of enantiopure asymmetric cis-2,5-disubstituted pyrrolidines: Facile access to chiral 10-heteroazatriquinanes

Convergent syntheses of LeX analogues

Convergent syntheses of Le^X analogues