Chiral phosphine-prolineamide as an organocatalyst in direct asymmetric aldol reactions

Mino, Takashi; Omura, Ayaka; Uda, Yukari; Wakui, Kazuya; Haga, Yuri; Sakamoto, Masami; Fujita, Tsutomu

doi:10.1016/j.tetasy.2011.11.021

Cited by 18 publications

(3 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The phosphine-catalyzed aldol reaction was updated by Mino and co-workers to an asymmetric version through the use of a chiral phosphine. 687 Treatment of electron-deficient aromatic aldehydes with cycloketones in the presence of 30 mol % of the chiral phosphine P113 , and 10 mol % of TFA as an additive, in DMF at 0 °C, led to chiral β -hydroxy ketones in 58–100% yield and with high diastereoselectivities (up to 98:2, dr) and enantioselectivities (60–97% ee) (Scheme 623). The reaction was sensitive to the electronic properties of the aromatic aldehydes and the structural properties of the ketones.…”

Section: Miscellaneous Phosphine Catalysismentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

View full text Add to dashboard Cite

The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon–carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita–Baylis–Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material—nucleophiles, dinucleophiles, electrophiles, and electrophile–nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon–carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon–carbon multiple bond–containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hüisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide–generating reactions.

show abstract

Section: Miscellaneous Phosphine Catalysismentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Mino and co‐workers described the chiral phosphine‐prolinamide 76 as an organocatalyst in asymmetric aldol reaction of 4‐nitrobezaldehyde 10 and cyclohexanone 11 , yielded anti ‐aldol product with excellent dr and ee (Scheme ) …”

Section: Prolinamide Catalysed Direct Asymmetric Aldol Reactionmentioning

confidence: 99%

“…Mino and co-workers described the chiral phosphineprolinamide 76 as an organocatalyst in asymmetric aldol reaction of 4-nitrobezaldehyde 10 and cyclohexanone 11, yielded anti-aldol product with excellent dr and ee (Scheme 29). [62] 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 Peddinti and co-workers synthesised the sugar-based prolinamides (79)(80)(81)(82) and tested for the asymmetric aldol reaction between 3-nitrobenzaldehyde (77) and cyclohexane (11) and catalyst (81) afforded in 96% yield and anti/syn (91:9) with 93% ee (Scheme 30). [63] Yang and co-workers reported the solvent effect on catalytic activity of prolinamides in asymmetric aldol reaction.…”

Section: Prolinamide Catalysed Direct Asymmetric Aldol Reactionmentioning

confidence: 99%

Prolinamide‐Catalysed Asymmetric Organic Transformations

2019

View full text Add to dashboard Cite

Proline was reported as an enantioselective organocatalyst for direct asymmetric aldol reaction in the early 1971 s by two independent groups of researchers and the reaction was called the Hajos‐Parrish‐Eder‐ Sauer Wiechert reaction. The breakthrough of enantioselective organocatalysis was demonstrated by List and co‐workers in 2000 for intermolecular aldol reaction between benzaldehydes and ketone using proline as a catalyst. After this report many researchers were applied the proline as a catalyst for other organic transformation. The proline has a carboxylic functional group which can easily convert to the amide and known as prolinamide. Prolinamides were found to be a better catalyst compared to proline in the most of cases. In this review article we are compiling the results of the prolinamides catalyzed asymmetric organic transformation with insight of the mechanism of catalysis.

show abstract

Lipase‐Catalyzed Stereoselective Cross‐Aldol Reaction Promoted by Water

et al. 2013

View full text Add to dashboard Cite

PPL, lipase from porcine pancreas, is first reported to catalyze direct asymmetric aldol reactions between aromatic aldehydes and cyclic ketones. More importantly, the catalytic activity of PPL was greatly promoted by a small quantity of water at 37 °C. A wide range of aromatic aldehydes reacted with cyclic ketones to provide the corresponding aldol products with high yields (up to 99 %) and moderate to good stereoselectivity (up to 90 % ee and 99:1 dr).

show abstract

Chiral phosphine-prolineamide as an organocatalyst in direct asymmetric aldol reactions

Cited by 18 publications

References 40 publications

Phosphine Organocatalysis

Phosphine Organocatalysis

Prolinamide‐Catalysed Asymmetric Organic Transformations

Lipase‐Catalyzed Stereoselective Cross‐Aldol Reaction Promoted by Water

Contact Info

Product

Resources

About