First asymmetrie synthesis of frans-3,4-dimethyl-4-arylpiperidines

Daniel P. Furkert; Stephen M. Husbands

doi:10.1021/ol0713988

First asymmetrie synthesis of frans-3,4-dimethyl-4-arylpiperidines

Daniel P. Furkert, Stephen M. Husbands

University of Bath

Research output: Contribution to journal › Article › peer-review

8 Citations (SciVal)

Abstract

The first asymmetric synthesis of the trans-3,4-dimethyl-4-arylpiperidine opioid antagonist scaffold is reported. C-3 stereochemistry was established via CBS reduction and stereoselective anti-S_N2′ cuprate displacement of the derived allylic phosphonate. The resultant vinyl bromide was then elaborated to the target compound by Suzuki coupling and frans-selective 4-methylation. Extension of this methodology should allow general enantioselective access to highly substituted piperidine ring systems.

Original language	English
Pages (from-to)	3769-3771
Number of pages	3
Journal	Organic letters
Volume	9
Issue number	19
DOIs	https://doi.org/10.1021/ol0713988
Publication status	Published - 13 Sept 2007

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0713988

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abstract = "The first asymmetric synthesis of the trans-3,4-dimethyl-4-arylpiperidine opioid antagonist scaffold is reported. C-3 stereochemistry was established via CBS reduction and stereoselective anti-SN2′ cuprate displacement of the derived allylic phosphonate. The resultant vinyl bromide was then elaborated to the target compound by Suzuki coupling and frans-selective 4-methylation. Extension of this methodology should allow general enantioselective access to highly substituted piperidine ring systems.",

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AB - The first asymmetric synthesis of the trans-3,4-dimethyl-4-arylpiperidine opioid antagonist scaffold is reported. C-3 stereochemistry was established via CBS reduction and stereoselective anti-SN2′ cuprate displacement of the derived allylic phosphonate. The resultant vinyl bromide was then elaborated to the target compound by Suzuki coupling and frans-selective 4-methylation. Extension of this methodology should allow general enantioselective access to highly substituted piperidine ring systems.

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First asymmetrie synthesis of frans-3,4-dimethyl-4-arylpiperidines

Abstract

ASJC Scopus subject areas

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