Organic Letters 2013-03-15

Unprecedented one-pot, domino tertiary alcohol protection-Michael type addition of halides to Morita-Baylis-Hillman adduct of isatin with RCOX/K2CO3: diastereoselective synthesis of oxindole appended β-halo esters.

Rajarethinam Solaiselvi, Ponnusamy Shanmugam, Asit Baran Mandal

Index: Org. Lett. 15(6) , 1186-9, (2013)

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Abstract

A facile method utilizing RCOX/K2CO3 as a novel reagent for conjugate addition of hydrogen halide, in addition to tertiary (3°)-hydroxyl protection that leads to the synthesis of functionalized β-halo Morita-Baylis-Hillman ester appended oxindoles, has been developed. The diastereoselective one-pot O-acylation-hydrohalogenation observed cannot otherwise be performed by treatment with hydrohalide. Deprotection of a 3°-hydroxyl protecting group has also been demonstrated by treatment with hydrochloric acid.