A novel domino reaction for the preparation of substituted non-racemic β-proline derivatives

A novel domino reaction for the preparation of substituted non-racemic β-proline derivatives

A novel domino reaction for the preparation of non-racemic β-proline derivatives is reported. The addition of a methyl 2-(oxetan-3-yl)acetate titanium enolate to chiral tert-butanesulfinyl ketimines followed by an intramolecular oxetane ring-opening provides the highly-substituted pyrrolidine ring s...

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Veröffentlicht in:Tetrahedron 2016-10, Vol.72 (40), p.6011-6020
Hauptverfasser: Gilbert, Eric J., Brunskill, Andrew, Cai, Jiaqiang, Cai, Yaxian, Chu, Xin-Jie, Dai, Xing, Hao, Jinsong, Kuethe, Jeffrey T., Lai, Zhong, Liu, Hong, Mu, Cuizhi, Qi, Yan, Scott, Jack D., Taoka, Brandon, Truong, Quang, Walsh, Shawn P., Wu, Wen-Lian, Cumming, Jared N.
Format: Artikel
Sprache:eng
Schlagworte:
Cascade chemical reactions
Derivatives
Domino reaction
Imines
Oxetane
tert-Butanesulfinyl ketimine
Tetrahedrons
Titanium
β-Proline
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Zusammenfassung:A novel domino reaction for the preparation of non-racemic β-proline derivatives is reported. The addition of a methyl 2-(oxetan-3-yl)acetate titanium enolate to chiral tert-butanesulfinyl ketimines followed by an intramolecular oxetane ring-opening provides the highly-substituted pyrrolidine ring systems with three contiguous stereogenic centers. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.08.017