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Paper | Regular issue | Vol 81, No. 2, 2010, pp.293-304
Published online, 13th November, 2009
DOI: 10.3987/COM-09-11850
Stereoselective Intramolecular Cyclization of Isopentenyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)

Jae-Eun Joo, Yu Mu, Yiu-Suk Lee, Yong-Shou Tian, Gyu-Jin Lee, and Won-Hun Ham*

*Department of Chemistry, Sung Kyun Kwan University, Suwon 440-746, Korea

Abstract

An efficient procedure was developed to synthesize oxazoline as key intermediate in the total synthesis of (+)-lactacystin using palladium(0)-catalyzed intramolecular cyclization of isopentenyl benzamide via a π–allylpalladium complex. A convenient and efficient method was developed for the synthesis of the optically pure α-amino-β-hydroxy acid.