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 beta-Halo Esters

作者：Solaiselvi Rajarethinam; Shanmugam Ponnusamy^*; Mandal Asit Baran

来源：Organic Letters, 2013, 15(6): 1186-1189.

DOI：10.1021/ol303554c

A facile method utilizing RDOX/K2CO3 as a novel reagent for conjugate addition of hydrogen halide, in addition to tertiary (3 degrees)-hydroxyl protection that leads to the synthesis of functionalized beta-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 degrees-hydroxyl protecting group has also been demonstrated by treatment with hydrochloric acid.

• 出版日期2013-3-15