Axially chiral dicarboxylic acid catalyzed asymmetric semipinacol rearrangement of cyclic [beta]-hydroxy-[alpha]-diazo esters

The development of axially chiral dicarboxylic acid catalyzed desymmetrizing asymmetric semipinacol rearrangement of symmetrically substituted six-membered cyclic [beta]-hydroxy-[alpha]-diazo esters is reported as a means to give chiral cycloheptanones with good enantioselectivities.

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Bibliographic Details
Published in:Tetrahedron 2012-09, Vol.68 (37), p.7630-7635
Main Authors: Hashimoto, Takuya, Isobe, Shingo, Callens, Cedric KA, Maruoka, Keiji
Format: Article
Language:English
Subjects:
Asymmetry
Dicarboxylic acids
Esters
Tetrahedrons
Online Access:Get full text
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Description
Summary:The development of axially chiral dicarboxylic acid catalyzed desymmetrizing asymmetric semipinacol rearrangement of symmetrically substituted six-membered cyclic [beta]-hydroxy-[alpha]-diazo esters is reported as a means to give chiral cycloheptanones with good enantioselectivities.
ISSN:0040-4020
DOI:10.1016/j.tet.2012.06.033