2004
DOI: 10.1002/anie.200353240
|View full text |Cite
|
Sign up to set email alerts
|

Enantioselective Mannich‐Type Reaction Catalyzed by a Chiral Brønsted Acid

Abstract: The enantioselective Mannich-type reaction of an enolate or an enolate anion equivalent with aldimines constitutes a useful method for the preparation of chiral b-amino carbonyl compounds, which are the precursors of biologically important compounds such as b-lactams and b-amino acids. The development of chiral catalysts for the asymmetric Mannichtype reaction has attracted the attention of synthetic organic chemists.[1] Although stoichiometric amounts of chiral acid were employed initially, [2] a number of e… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1

Citation Types

1
572
1
24

Year Published

2007
2007
2022
2022

Publication Types

Select...
6
3

Relationship

0
9

Authors

Journals

citations
Cited by 1,534 publications
(598 citation statements)
references
References 58 publications
1
572
1
24
Order By: Relevance
“…Since pioneering works reported in 2004 by Terada [63] and Akiyama [64], chiral phosphoric acids have rapidly emerged as a new potent class of Brønsted acid catalysts with remarkable synthetic power owing to its continuous application in the development of new organocatalytic methodologies and resulting in a significant expansion of this field [65] (Fig XII.5). Proof of this substantial progress is the employment of such privileged class of Brønsted acids in the total syntheses of significant compounds as, for instance: ()-arboricine A [66], (S)-anabasine [67], monastrol [68], ()-zampanolide [69], (+)-galipinine [70,71], (+)-cuspareine [70], ()-angusturine [70,72], and torcetrapib [73] (Fig XII.6).…”
Section: Xii31 Phosphoric Acidsmentioning
confidence: 99%
“…Since pioneering works reported in 2004 by Terada [63] and Akiyama [64], chiral phosphoric acids have rapidly emerged as a new potent class of Brønsted acid catalysts with remarkable synthetic power owing to its continuous application in the development of new organocatalytic methodologies and resulting in a significant expansion of this field [65] (Fig XII.5). Proof of this substantial progress is the employment of such privileged class of Brønsted acids in the total syntheses of significant compounds as, for instance: ()-arboricine A [66], (S)-anabasine [67], monastrol [68], ()-zampanolide [69], (+)-galipinine [70,71], (+)-cuspareine [70], ()-angusturine [70,72], and torcetrapib [73] (Fig XII.6).…”
Section: Xii31 Phosphoric Acidsmentioning
confidence: 99%
“…Since Akiyama 21 and Terada 22 independently accomplished an innovative approach to the development of chiral BINOL derived phosphoric acid catalysts in 2004, it soon became clear that they possessed tremendous potential to activate electrophiles towards nucleophilic attack in asymmetric catalysis. 23 Although many successful enantioselective addition reactions to imines have been achieved with these Brønsted acids, the utility of these acids to the activation of other functional groups are somewhat limited due to relatively lower reactivities of these Brønsted acids.…”
Section: Chiral N Tri Yl Oxo Phosphoramidesmentioning
confidence: 99%
“…The substituents of 3,3 position of BINOL, which have been developed by many researchers, are shown in Table 6. 21,22,26,32,38 In the enantioselective Mukaiyama aldol reaction, the bulky substituent, 9 anthracenyl, at the 4 position of 3,3 aryl substituent of the BINOL improved both diastereoselectivity and enantioselectivity.…”
Section: Chiral N Tri Yl Thio and Seleno Phosphoramidesmentioning
confidence: 99%
“…[1][2][3] Binaphthyl-containing polymers such as polyarylenes, polyimides, and polycarbonates have been much reported, which have been applied to polymeric catalysts and so on. [4][5][6][7][8] We have also reported the syntheses of optically active aromatic polyketones bearing 2,2 0 -dioxy-1,1 0 -binaphthyl-6,6 0 -diyl units via nucleophilic aromatic substitution polymerization and nickel complex-mediated aromatic coupling polymerization.…”
Section: 2mentioning
confidence: 99%