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Wiley-VCH Verlag, ChemInform, 29(46), p. no-no, 2015

DOI: 10.1002/chin.201529138

Elsevier, Tetrahedron, 15(71), p. 2210-2221

DOI: 10.1016/j.tet.2015.02.083

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Studies towards development of asymmetric double-Mannich reactions of chiral 2-oxocyclohexanecarboxylate derivatives with bis(aminol)ethers

Journal article published in 2015 by Kevin John Sparrow, Sarah Carley, Tilo Söhnel, David Barker, Margaret A. Brimble ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

A range of chiral ester and chiral imide derivatives of 2-oxocyclohexanecarboxylic acid were utilized in double-Mannich reactions with bis(aminol)ethers to develop an asymmetric synthesis of azabicyclo[3.3.1]nonanes. An improved method for the double-Mannich reaction of β-ketoesters and bis(aminol)ethers using sub-stoichiometric quantities of a Lewis acid was developed. Additionally, a sequential, double-Mannich approach was investigated incorporating chiral auxiliaries into N,O-acetals. The use of oxazolidinone auxiliaries afforded the best yields and diastereoselectivities enabling separation of the resulting diastereomers of the azabicyclo[3.3.1]nonanes.