Concepedia

Diastereoconvergent Synthesis of <i>trans</i>-5-Hydroxy-6-Substituted-2-Piperidinones by Addition–Cyclization–Deprotection Process

Chang‐Mei Si, Wei Huang, Zhen‐Ting Du, Bang‐Guo Wei, Guo‐Qiang Lin

Organic Letters · 2014 · 55 citations · 45 references

DOI

Concepts

Abstract

A diastereoselective one-pot approach to access trans-5-hydroxy-6-substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by α-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.

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