Concepedia

A novel AlEt3-promoted tandem reductive rearrangement of 1-benzyloxy-2,3-epoxides: new route to 2-quaternary 1,3-diol unitsElectronic supplementary information (ESI) available: experimental section. See http://www.rsc.org/suppdata/cc/b2/b209948a/

De Run Li, Wu Jiong Xia, Yong Qiang Tu, Fu Min Zhang, Lei Shi

Chemical Communications · 2003 · 16 citations · 10 references

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Abstract

A novel and highly stereoselective tandem rearrangement-reduction reaction of 1-benzyloxy-2,3-epoxide, under the promotion of triethylaluminum (AlEt3), has been developed to construct a quaternary stereocenter and the hydroxymethyl attached to the carbon center in one-step.

References

10

Self‐Regeneration of Stereocenters (SRS)—Applications, Limitations, and Abandonment of a Synthetic Principle

Dieter Seebàch, Andrea Rolf Sting, Matthias Hoffmann · Angewandte Chemie International Edition in English · 1996 · 482 citations

, , +9

Allylic oxidation of olefins with chromium trioxide pyridine complex

William G. Dauben, Milton E. Lorber, Dwight S. Fullerton · The Journal of Organic Chemistry · 1969 · 230 citations

, , +5

Novel Asymmetric Alkylation of Aromatic Aldehydes with Triethylaluminum Catalyzed by Titanium·(1,1‘-bi-2-naphthol) and Titanium·(5,5‘,6,6‘,7,7‘,8,8‘-octahydro-1,1‘- bi-2-naphthol) Complexes

Albert S. C. Chan, Fuyao Zhang, Chiu‐Wing Yip · Journal of the American Chemical Society · 1997 · 142 citations

, , +10

Organoaluminum-promoted rearrangement of epoxy silyl ethers to .beta.-siloxy aldehydes

Keiji Maruoka, Takashi Ooi, Hisashi Yamamoto · Journal of the American Chemical Society · 1989 · 134 citations

, , +5

Organoaluminum-catalyzed rearrangement of epoxides a facile route to the synthesis of optically active β-siloxy aldehydes

Keiji Maruoka, Takashi Ooi, Shigeru Nagahara et al. · Tetrahedron · 1991 · 100 citations

, , +8