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

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

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 demonstra...

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Veröffentlicht in:Organic letters 2014-08, Vol.16 (16), p.4328-4331
Hauptverfasser: Si, Chang-Mei, Huang, Wei, Du, Zhen-Ting, Wei, Bang-Guo, Lin, Guo-Qiang
Format: Artikel
Sprache:eng
Schlagworte:
Cyclization
Molecular Structure
Piperidines - chemical synthesis
Piperidines - chemistry
Piperidones - chemical synthesis
Piperidones - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5020812