F₃B · OEt₂‐Promoted Intramolecular Si to C Phenyl Group Migration: A Highly Diastereoselective Synthesis of (4S,5S)‐4‐Hydroxy‐5‐phenyl‐2‐pyrrolidinone

Liang‐Xian Liu Department of Chemistry and Biology, Ganan Teachers' College, Ganzhou, Jiangxi, China; Department of Chemistry and the Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, China

Pei‐Qiang Huang Department of Chemistry and the Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, ChinaCorrespondence[email protected]

Abstract

A highly diastereoselective approach to N‐protected cis‐(4S,5S)‐4‐hydroxy‐5‐phenyl‐2‐pyrrolidinone is reported. The key step is a boron trifluoride etherate–promoted chemoselective intramolecular Si→C phenyl group migration.

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Acknowledgment

The authors are grateful to the Natural Science Foundation (NSF) of China (20272048; 203900505) and the Ministry of Education (Key Project 104201) for financial support.

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F₃B · OEt₂‐Promoted Intramolecular Si to C Phenyl Group Migration: A Highly Diastereoselective Synthesis of (4S,5S)‐4‐Hydroxy‐5‐phenyl‐2‐pyrrolidinone

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F3B · OEt2‐Promoted Intramolecular Si to C Phenyl Group Migration: A Highly Diastereoselective Synthesis of (4S,5S)‐4‐Hydroxy‐5‐phenyl‐2‐pyrrolidinone

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F₃B · OEt₂‐Promoted Intramolecular Si to C Phenyl Group Migration: A Highly Diastereoselective Synthesis of (4S,5S)‐4‐Hydroxy‐5‐phenyl‐2‐pyrrolidinone