N-Pyrrolidine-based α/β-peptides incorporating ABOC, a constrained bicyclic β-amino acid, for asymmetric aldol reaction catalysis

Pierre Milbeo; Kelly Maurent; Laure Moulat; Aurélien Lebrun; Claude Didierjean; Emmanuel Aubert; Jean Martinez; Monique Calmès

doi:10.1016/j.tet.2016.02.027

N-Pyrrolidine-based α/β-peptides incorporating ABOC, a constrained bicyclic β-amino acid, for asymmetric aldol reaction catalysis

Tetrahedron ◽

10.1016/j.tet.2016.02.027 ◽

2016 ◽

Vol 72 (13) ◽

pp. 1706-1715 ◽

Cited By ~ 10

Author(s):

Pierre Milbeo ◽

Kelly Maurent ◽

Laure Moulat ◽

Aurélien Lebrun ◽

Claude Didierjean ◽

...

Keyword(s):

Amino Acid ◽

Aldol Reaction ◽

Asymmetric Aldol ◽

Asymmetric Aldol Reaction

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Synthesis of a Biphenyl-Based Axially Chiral Amino Acid as a Highly Efficient Catalyst for the Direct Asymmetric Aldol Reaction.

ChemInform ◽

10.1002/chin.200705076 ◽

2007 ◽

Vol 38 (5) ◽

Author(s):

Taichi Kano ◽

Osamu Tokuda ◽

Keiji Maruoka

Keyword(s):

Amino Acid ◽

Aldol Reaction ◽

Efficient Catalyst ◽

Asymmetric Aldol ◽

Highly Efficient ◽

Axially Chiral ◽

Asymmetric Aldol Reaction

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ChemInform Abstract: Efficient Synthesis of β-Hydroxy-α-amino Acid Derivatives via Direct Catalytic Asymmetric Aldol Reaction of α-Isothiocyanato Imide with Aldehydes.

ChemInform ◽

10.1002/chin.201103131 ◽

2010 ◽

Vol 42 (3) ◽

pp. no-no

Author(s):

Xiaohong Chen ◽

Yin Zhu ◽

Zhen Qiao ◽

Mingsheng Xie ◽

Lili Lin ◽

...

Keyword(s):

Amino Acid ◽

Aldol Reaction ◽

Amino Acid Derivatives ◽

Efficient Synthesis ◽

Asymmetric Aldol ◽

Asymmetric Aldol Reaction ◽

Catalytic Asymmetric

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Efficient Synthesis of β-Hydroxy-α-Amino Acid Derivatives via Direct Catalytic Asymmetric Aldol Reaction of α-Isothiocyanato Imide with Aldehydes

Chemistry - A European Journal ◽

10.1002/chem.201000284 ◽

2010 ◽

Vol 16 (33) ◽

pp. 10124-10129 ◽

Cited By ~ 32

Author(s):

Xiaohong Chen ◽

Yin Zhu ◽

Zhen Qiao ◽

Mingsheng Xie ◽

Lili Lin ◽

...

Keyword(s):

Amino Acid ◽

Aldol Reaction ◽

Amino Acid Derivatives ◽

Efficient Synthesis ◽

Asymmetric Aldol ◽

Asymmetric Aldol Reaction ◽

Catalytic Asymmetric

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Design of an Axially Chiral Amino Acid with a Binaphthyl Backbone as an Organocatalyst for a Direct Asymmetric Aldol Reaction

Angewandte Chemie International Edition ◽

10.1002/anie.200500408 ◽

2005 ◽

Vol 44 (20) ◽

pp. 3055-3057 ◽

Cited By ~ 120

Author(s):

Taichi Kano ◽

Jun Takai ◽

Osamu Tokuda ◽

Keiji Maruoka

Keyword(s):

Amino Acid ◽

Aldol Reaction ◽

Asymmetric Aldol ◽

Axially Chiral ◽

Asymmetric Aldol Reaction

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Design of an Axially Chiral Amino Acid with a Binaphthyl Backbone as an Organocatalyst for a Direct Asymmetric Aldol Reaction.

ChemInform ◽

10.1002/chin.200538042 ◽

2005 ◽

Vol 36 (38) ◽

Author(s):

Taichi Kano ◽

Jun Takai ◽

Osamu Tokuda ◽

Keiji Maruoka

Keyword(s):

Amino Acid ◽

Aldol Reaction ◽

Asymmetric Aldol ◽

Axially Chiral ◽

Asymmetric Aldol Reaction

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ChemInform Abstract: N-Pyrrolidine-Based α/β-Peptides Incorporating ABOC, a Constrained Bicyclic β-Amino Acid, for Asymmetric Aldol Reaction Catalysis.

ChemInform ◽

10.1002/chin.201628023 ◽

2016 ◽

Vol 47 (28) ◽

Author(s):

Pierre Milbeo ◽

Kelly Maurent ◽

Laure Moulat ◽

Aurelien Lebrun ◽

Claude Didierjean ◽

...

Keyword(s):

Amino Acid ◽

Aldol Reaction ◽

Asymmetric Aldol ◽

Asymmetric Aldol Reaction

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Design of an Axially Chiral Amino Acid with a Binaphthyl Backbone as an Organocatalyst for a Direct Asymmetric Aldol Reaction

Angewandte Chemie ◽

10.1002/ange.200500408 ◽

2005 ◽

Vol 117 (20) ◽

pp. 3115-3117 ◽

Cited By ~ 24

Author(s):

Taichi Kano ◽

Jun Takai ◽

Osamu Tokuda ◽

Keiji Maruoka

Keyword(s):

Amino Acid ◽

Aldol Reaction ◽

Asymmetric Aldol ◽

Axially Chiral ◽

Asymmetric Aldol Reaction

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ChemInform Abstract: Amino Acid Salts Catalyzed Asymmetric Aldol Reaction of Tryptanthrin: A Straightforward Synthesis of Phaitanthrin A (V) and Its Derivatives.

ChemInform ◽

10.1002/chin.201407184 ◽

2014 ◽

Vol 45 (7) ◽

pp. no-no

Author(s):

Guowei Kang ◽

Zhenli Luo ◽

Chongxing Liu ◽

Hang Gao ◽

Quanquan Wu ◽

...

Keyword(s):

Amino Acid ◽

Aldol Reaction ◽

Asymmetric Aldol ◽

Asymmetric Aldol Reaction ◽

Amino Acid Salts ◽

Acid Salts

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Amino Acid Mediated Intramolecular Asymmetric Aldol Reaction to Construct a New Chiral Bicyclic Enedione Containing a Seven-Membered Ring: Remarkable Inversion of Enantioselectivity Compared to the Six-Membered Ring Example

The Journal of Organic Chemistry ◽

10.1021/jo061824n ◽

2007 ◽

Vol 72 (1) ◽

pp. 123-131 ◽

Cited By ~ 50

Author(s):

Takashi Nagamine ◽

Kohei Inomata ◽

Yasuyuki Endo ◽

Leo A. Paquette

Keyword(s):

Amino Acid ◽

Aldol Reaction ◽

Membered Ring ◽

Asymmetric Aldol ◽

Asymmetric Aldol Reaction

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The smallest organocatalyst in highly enantioselective direct aldol reaction in wet solvent-free conditions

RSC Advances ◽

10.1039/c4ra02690j ◽

2014 ◽

Vol 4 (46) ◽

pp. 24311-24315 ◽

Cited By ~ 21

Author(s):

Sudipto Bhowmick ◽

Sunita S. Kunte ◽

Kartick C. Bhowmick

Keyword(s):

Amino Acid ◽

Room Temperature ◽

Aldol Reaction ◽

Aromatic Aldehydes ◽

Solvent Free ◽

Natural Amino Acid ◽

Asymmetric Aldol ◽

Direct Aldol Reaction ◽

Solvent Free Conditions ◽

Asymmetric Aldol Reaction

The catalytic efficacy of the smallest organocatalyst, l-proline hydrazide, prepared from a cheaply available natural amino acid, such as l-proline, was studied for the direct asymmetric aldol reaction of various ketones with aromatic aldehydes at room temperature in the presence of several acid additives.

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