Dr. Taichi Kusakabe, Takeo Takahashi, Rong Shen, Ayumi Ikeda, Yogesh Daulat Dhage, Dr. Yuichro Kanno, Prof. Dr. Yoshio Inouye, Prof. Dr. Hiroaki Sasai, Prof. Dr. Tomoyuki Mochida and Prof. Dr. Keisuke Kato Carbonylation of Propargyl Carbamates with Palladium(II) Bisoxazoline Catalysts: Efficient Synthesis of 5-Methoxy-3(2H)-furanones Angewandte Chemie International Edition 52
Version of Record online: 20 JUN 2013 | DOI: 10.1002/anie.201303684
Palladium and CO: Carbonylation of 1 with [Pd(tfa)2(±)-L1] (tfa=trifluoroacetate) affords the spirofuranone 2 with inversion of the stereochemistry at C17 in 96 % yield. C17-epi-1 also gave the same product 2 with retention of the stereochemistry at C17. Labelling studies show that 13CO was incorporated into the C5′ position of the furanone ring. The first asymmetric version of this new reaction was achieved.
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