A C2-symmetric chiral amino diol (1R,5R)-3-aza-3-benzyl-1,5-diphenyl pentan-1,5-diol [(R,R)-I] has been synthesised by a modified procedure. The heterobimetallic catalyst [I2-AI-Li] obtained by reaction of the amino diol [(R,R)-I] with LiAlH4, promotes asymmetric Michael addition of malonic esters and thiophenols to α,β-unsaturated compounds with high enantiomeric excess.

G. Manickam

Govindarajan Sundararajan

alkanediol derivative

cycloalkane derivative

malonic acid derivative

article

column chromatography

DRUG PURIFICATION

drug synthesis

in vitro study

Mass spectrometry

methodology

Nuclear magnetic resonance spectroscopy

priority journal

reaction analysis

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

A new C2-symmetric heterobimetallic complex as a promoter for asymmetric Michael addition reactions

Tetrahedron Asymmetry

A new Ti(IV) complex obtained from the C2-symmetric amino diol (1R,5R)-3-aza-3-benzyl-1,5-diphenyl pentan-1,5-diol,(1R,5R)-1, is used effectively as a Lewis acid promoter in asymmetric Diels-Alder reactions. Using various Evans' oxazolidinones as dienophiles and cyclopentadiene as the diene high yields of the adducts with moderate enantioselectivity, under different reaction conditions are achieved. The effects of solvent, temperature and ligand on the enantioselectivity of the Diels-Alder products are reported. Molecular modelling studies provide an understanding of the diastereofacial selectivity of the Diels-Alder reactions. Asymmetric carbonyl-ene reactions between various glyoxylate esters and α-methyl styrene are also described.

Asymmetric Diels-Alder and ene reactions promoted by a Ti(IV) complex bearing a C2-symmetric tridentate ligand

The C2-symmetric amino diol, (1R,5R)-3-aza-3-benzyl-1,5-diphenyl pentan-1, 5-diol, 1 [(R,R)-1] reacts with LiAlH4 to give the heterobimetallic complex 2 of the composition [(12-Al)Li]. Complex 2 was characterised by 1H-, 13C-, 27Al- and 7Li-NMR spectral data. Also, 2 when used in catalytic amounts accelerates Michael addition of malonates and thiophenol to α,β-unsaturated compounds like aldehydes, ketones, cyano and nitro compounds with high yield. Asymmetric induction in the Michael adducts has also been observed when a enantiomerically pure catalyst 2 was employed.

Tetrahedron

Lithium bis[(1R,5R)-3-aza-3-benzyl-1,5-diphenylpentan-1,5-diolato]- aluminium - A new heterobimetallic catalyst for Michael addition reactions

Journal of the American Chemical Society

A modular approach for ligand design for asymmetric allylic alkylations via enantioselective palladium-catalyzed ionizations

Chemical Reviews

C2 symmetry and asymmetric induction

Canadian Journal of Chemistry

Cyclic nitronates from the diastereoselective addition of 1-trimethylsilyloxycyclohexene to nitroolefins. Starting materials for stereoselective Henry reactions and 1,3-dipolar cycloadditions

Journal of the Chemical Society, Perkin Transactions 1

Asymmetric induction in the Michael reaction by means of chiral phase-transfer catalysts derived from cinchona and ephedra alkaloids

The Journal of Organic Chemistry

Cycloalk-2-enones and α,β,α',β'-Cycloalkadienones. A. Synthesis. B. On the Direction of Bromination of 2-Substituted Cycloalkanones and Their Ketals

Journal	Tetrahedron Asymmetry
ISSN	09574166
Open Access	No