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Synlett 2008(13): 1946-1948  
DOI: 10.1055/s-2008-1077959
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Baylis-Hillman Reaction of Cyclic Enones with Arenecarbaldehydes and N-Arylidene-4-methylbenzenesulfonamides by Using NAP-MgO

M. Lakshmi Kantam*a, L. Chakrapania, B. M. Choudaryb
a Inorganic & Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160921; e-Mail: mlakshmi@iict.res.in;
b Ogene Systemes (I) Private Limited, Balanagar, Hyderabad 500037, India
Further Information

Publication History

Received 11 January 2008
Publication Date:
15 July 2008 (online)

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Abstract

Baylis-Hillman reaction of cyclic enones with arene­carbaldehydes and N-arylidene-4-methylbenzenesulfonamides under mild conditions by using nanocrystalline MgO (NAP-MgO) afforded the Baylis-Hillman adducts in moderate to good yields with higher selectivity than the corresponding aldol products.

Keywords

Baylis-Hillman reaction - cyclic enones - NAP-MgO - heterogeneous - solid base

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General Procedure for the Baylis-Hillman Reaction of Cyclic Enones using NAP-MgO: To a dried 25-mL round-bottomed flask charged with NAP-MgO (25 mg) were added MeOH (3 mL), followed by aldehyde (0.5 mmol) and cyclic enone (1 mmol) at r.t. The reaction was monitored by TLC. After completion of the reaction, the catalyst was separated by centrifuging the reaction mixture, and the supernatant liquid was concentrated to afford the crude product. Column chromatography of the crude (silica gel, 60-120 mesh, EtOAc-hexane, varying proportions) gave the corresponding Baylis-Hillman adduct. All the products are known compounds, which were identified by IR, ¹H NMR spectroscopy, and mass spectrometry.