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Synthesis of novel chiral bithiophenebased phosphine oxides as Lewis bases in organocatalytic stereoselective reactions

100%

Rossi S., Benaglia M., Cirilli R., Benincori T.

Asymmetric Catalysis

2015

vol. 2

issue 1

Novel enantiomerically pure tetramethylbithiophene diphosphine oxides (tetraMe-BITIOPO) featuring differently substituted aromatic rings at the phosphorous atoms were synthesized, fully characterized and isolated in enantiomerically pure form. The new Lewis bases were tested as organocatalysts in two different reactions involving trichlorosilyl compounds. The introduction of electron donating substituents on the aromatic rings connected to the phosphine oxide groups positively affected the chemical and stereochemical catalytic efficiency of these ligands. The new catalysts were able to promote the allylation of aldehydes with allyltrichlorosilane in up to 76% yield and up to 86% enantiomeric excess (ee), and the direct aldol reaction to afford β-hydroxy ketones in high diastereoselectivity (up to 88:12 anti:syn ratio) and up to 72% ee.

Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides and Acrolein

86%

Ugarriza I., Uria U., Reyes E., Carrillo L., Vicario J. L.

Asymmetric Catalysis

2015

vol. 2

issue 1

The [3+2]-cycloaddition reaction between acrolein and in situ generated acyclic azomethine ylides promoted by a chiral secondary amine to generate C-3 unsubstituted pyrrolidines has been studied in detail. Optimum conditions involve the use of the cheap and readily available l-Proline as catalyst to afford the pyrrolidine cycloadduct with complete diastereomeric control and up to 80% enantiomeric control.

One-pot synthesis of(R)-convolutamydineA involvingin situchiral organocatalyst formation

86%

Wei S., Schmid B., Macaev F. Z., Curlat S. N., 1, Malkov A. V., Tsogoeva S. B.

Asymmetric Catalysis

2015

vol. 2

issue 1

The application of a convenient one-pot synthetic strategy, utilizing an in situ formed organocatalyst, to the enantioselective synthesis of anti-leukaemia agent (R)-convolutamydine A has been demonstrated.

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3 Asymmetric Catalysis

3 2015

1 1

1 Benaglia M.

1 Benincori T.

1 Carrillo L.

1 Cirilli R.

1 Curlat S. N.

1 Macaev F. Z.

1 Malkov A. V.

1 Reyes E.

1 Rossi S.

1 Schmid B.

1 Tsogoeva S. B.

1 Ugarriza I.

1 Uria U.

1 Vicario J. L.

1 Wei S.

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Synthesis of novel chiral bithiophenebased phosphine oxides as Lewis bases in organocatalytic stereoselective reactions

Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides and Acrolein

One-pot synthesis of(R)-convolutamydineA involvingin situchiral organocatalyst formation