3-Allyl-3-hydroxyoxindoles were synthesized in very good enantio- (up to 97% ee) and diastereoselectivities (dr up to 7.6:1) with contiguous quaternary and tertiary stereogenic centers by employing tartrate derived bi(oxazoline) in Pd-catalyzed allylation of 3-OBoc-oxindole. Synthetic utility of 3-allyl-3-hydroxyoxindole was demonstrated by synthesizing a highly substituted spiro(oxindole-3,2′-tetrahydrofuran) derivative in good yield and stereoselectivity. © 2015 American Chemical Society.

Venkitasamy Kesavan

Department Of Biotechnology

Samydurai Jayakumar

Nandarapu Kumarswamyreddy

Muthuraj Prakash

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

Organic Letters

3-Alkynyl-3-OBoc oxindoles underwent Cu(II) mediated Friedel-Crafts alkylation with indoles and phenols to yield of structurally diverse 3-alkynyl-3-indole/phenol-oxindole derivatives. The synthetic application of alkylated phenol derivatives were further demonstrated to biologically important new class of chromene fused spirooxindoles through intramolecular metal-free iodocyclization under mild reaction conditions with broad substrate scope in very good yields. © 2018 Elsevier Ltd

Tetrahedron Letters

Efficient synthesis of highly functionalized indole and phenol containing 3,3′-disubstituted oxindoles and chromene fused spirooxindoles

The synthesis of highly functionalized spirocarbocyclic oxindoles was accomplished for the first time, using a Hauser annulation strategy. A reaction between methyleneindolinones and arylsulfonylphthalides catalyzed by cesium carbonate gave access to a new class of biologically important spiro[indoline-3,2′-naphthalene] derivatives in very good yields. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

European Journal of Organic Chemistry

Efficient Synthesis of Highly Functionalized Spirocarbocyclic Oxindoles through Hauser Annulation

A new bifunctional squaramide organocatalyst derived from l-proline mediated the first enantioselective synthesis of dihydrospiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives in excellent enantioselectivity by reacting pyrazolones with isatylidine β,γ-unsaturated α-ketoester. This new catalyst outperformed widely used thioureas and squaramides in inducing enantioselectivity. © 2016 American Chemical Society.

Journal	Data powered by TypesetOrganic Letters
Publisher	Data powered by TypesetAmerican Chemical Society
ISSN	15237060
Open Access	No