Lewis Acid Promoted Highly Diastereoselective Petasis Borono-Mannich Reaction: Efficient Synthesis of Optically Active β,γ-Unsaturated α-Amino Acids

Yi Li; Ming-Hua Xu

doi:10.1021/ol300581n

Lewis Acid Promoted Highly Diastereoselective Petasis Borono-Mannich Reaction: Efficient Synthesis of Optically Active β,γ-Unsaturated α-Amino Acids

Organic Letters ◽

10.1021/ol300581n ◽

2012 ◽

Vol 14 (8) ◽

pp. 2062-2065 ◽

Cited By ~ 51

Author(s):

Yi Li ◽

Ming-Hua Xu

Keyword(s):

Amino Acids ◽

Lewis Acid ◽

Mannich Reaction ◽

Optically Active ◽

Efficient Synthesis

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ChemInform Abstract: Lewis Acid Promoted Highly Diastereoselective Petasis Borono-Mannich Reaction: Efficient Synthesis of Optically Active β,γ-Unsaturated α-Amino Acids.

ChemInform ◽

10.1002/chin.201234180 ◽

2012 ◽

Vol 43 (34) ◽

pp. no-no

Author(s):

Yi Li ◽

Ming-Hua Xu

Keyword(s):

Amino Acids ◽

Lewis Acid ◽

Mannich Reaction ◽

Optically Active ◽

Efficient Synthesis

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An Efficient Synthesis of Optically Active α-(t-Butoxycarbonylamino)-aldehydes from α-Amino Acids

Synthesis ◽

10.1055/s-1983-30471 ◽

1983 ◽

Vol 1983 (08) ◽

pp. 676-678 ◽

Cited By ~ 299

Author(s):

Jean-Alain Fehrentz ◽

Bertrand Castro

Keyword(s):

Amino Acids ◽

Optically Active ◽

Efficient Synthesis

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ChemInform Abstract: Cyclopropyl Building Blocks for Organic Synthesis. Part 14. Optically Active Oxazolidinones as Michael Donors for the Short and Efficient Synthesis of β-Amino Acids Containing a Cyclopropane Ring.

ChemInform ◽

10.1002/chin.199323265 ◽

2010 ◽

Vol 24 (23) ◽

pp. no-no

Author(s):

M. ES-SAYED ◽

C. GRATKOWSKI ◽

N. KRASS ◽

A. I. MEYERS ◽

A. DE MEIJERE

Keyword(s):

Amino Acids ◽

Organic Synthesis ◽

Cyclopropane Ring ◽

Building Blocks ◽

Optically Active ◽

Efficient Synthesis

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Optically active oxazolidinones as Michael donors for the short and efficient synthesis of β-amino acids containing a cyclopropane ring

Tetrahedron Letters ◽

10.1016/s0040-4039(00)60569-5 ◽

1993 ◽

Vol 34 (2) ◽

pp. 289-292 ◽

Cited By ~ 21

Author(s):

Mazen Es-Sayed ◽

Corinna Gratkowski ◽

Norbert Krass ◽

Albert I. Meyers ◽

Armin de Meijere

Keyword(s):

Amino Acids ◽

Cyclopropane Ring ◽

Optically Active ◽

Efficient Synthesis

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Inside Cover: Lewis-Acid-Catalyzed Intramolecular Aza-Friedel-Crafts Reaction ofN-tert-Butanesulfinyl Imines: Efficient Synthesis of Optically Active 9-Aminofluorene Derivatives (Asian J. Org. Chem. 1/2013)

Asian Journal of Organic Chemistry ◽

10.1002/ajoc.201390001 ◽

2013 ◽

Vol 2 (1) ◽

pp. 2-2 ◽

Cited By ~ 1

Author(s):

Yi Li ◽

Ming-Hua Xu

Keyword(s):

Lewis Acid ◽

Optically Active ◽

Efficient Synthesis ◽

Acid Catalyzed

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Stereodivergent Mannich reaction of bis(trimethylsilyl)ketene acetals with N-tert-butanesulfinyl imines by Lewis acid or Lewis base activation, a one-pot protocol to obtain chiral β-amino acids

Organic & Biomolecular Chemistry ◽

10.1039/c7ob01853c ◽

2017 ◽

Vol 15 (36) ◽

pp. 7705-7709 ◽

Cited By ~ 8

Author(s):

Margarita Cantú-Reyes ◽

Isabel Alvarado-Beltrán ◽

Ricardo Ballinas-Indilí ◽

Cecilio Álvarez-Toledano ◽

Marcos Hernández-Rodríguez

Keyword(s):

Amino Acids ◽

Lewis Acid ◽

Mannich Reaction ◽

Lewis Base ◽

One Pot ◽

Ketene Acetals

Synthesis of chiral β2,2,3-amino acids. Either Lewis acid or Lewis base promote the reaction, surprisingly, each activation afford different enantiomer.

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Synthesis of racemic .alpha.-amino carboxamides via Lewis acid-mediated reactions of .alpha.-methoxyglycinamide derivatives with allylsilanes: enzymic resolution to optically active .alpha.-amino acids

The Journal of Organic Chemistry ◽

10.1021/jo00051a019 ◽

1992 ◽

Vol 57 (25) ◽

pp. 6769-6778 ◽

Cited By ~ 30

Author(s):

Eric C. Roos ◽

Hendrik H. Mooiweer ◽

Henk Hiemstra ◽

W. Nico Speckamp ◽

Bernard Kaptein ◽

...

Keyword(s):

Amino Acids ◽

Lewis Acid ◽

Optically Active

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ChemInform Abstract: Pd(II)-Catalyzed Alkylation of Unactivated C(sp3)-H Bonds: Efficient Synthesis of Optically Active Unnatural α-Amino Acids.

ChemInform ◽

10.1002/chin.201407036 ◽

2014 ◽

Vol 45 (7) ◽

pp. no-no

Author(s):

Kai Chen ◽

Fang Hu ◽

Shuo-Qing Zhang ◽

Bing-Feng Shi

Keyword(s):

Amino Acids ◽

Optically Active ◽

Efficient Synthesis

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Lewis-Acid-Catalyzed Intramolecular Aza-Friedel-Crafts Reaction ofN-tert-Butanesulfinyl Imines: Efficient Synthesis of Optically Active 9-Aminofluorene Derivatives

Asian Journal of Organic Chemistry ◽

10.1002/ajoc.201200161 ◽

2013 ◽

Vol 2 (1) ◽

pp. 50-53 ◽

Cited By ~ 8

Author(s):

Yi Li ◽

Ming-Hua Xu

Keyword(s):

Lewis Acid ◽

Optically Active ◽

Efficient Synthesis ◽

Acid Catalyzed

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ChemInform Abstract: Synthesis of Racemic α-Amino Carboxamides via Lewis Acid- Mediated Reactions of α-Methoxyglycinamide Derivatives with Allylsilanes: Enzymatic Resolution to Optically Active α-Amino Acids.

ChemInform ◽

10.1002/chin.199318168 ◽

2010 ◽

Vol 24 (18) ◽

pp. no-no

Author(s):

E. C. ROOS ◽

H. H. MOOIWEER ◽

H. HIEMSTRA ◽

W. N. SPECKAMP ◽

B. KAPTEIN ◽

...

Keyword(s):

Amino Acids ◽

Lewis Acid ◽

Optically Active ◽

Enzymatic Resolution

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