A Combination of Metal and Organic Catalysis: Highly Diastereo- and Enantioselective Construction of Fluorinated 2-Aminocyclopenta[b]pyran Derivatives

Jiahuan Peng; Bo Liang Zhao; Da Ming Du

doi:10.1002/adsc.201500744

A Combination of Metal and Organic Catalysis: Highly Diastereo- and Enantioselective Construction of Fluorinated 2-Aminocyclopenta[b]pyran Derivatives

Jiahuan Peng, Bo Liang Zhao, Da Ming Du^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

14 Citations (Scopus)

Abstract

An efficient highly diastereo- and enantioselective protocol to access optically pure fluorine-containing 2-amino-cyclopenta[b]pyran derivatives using Lewis acid catalysis and organocatalysis sequence has been developed. The corresponding products could be obtained in good to excellent yields with good to excellent diastereoselectivity and enantioselectivity (up to 99:1 dr, >99% ee).

Original language	English
Pages (from-to)	3639-3647
Number of pages	9
Journal	Advanced Synthesis and Catalysis
Volume	357
Issue number	16-17
DOIs	https://doi.org/10.1002/adsc.201500744
Publication status	Published - 16 Nov 2015

Keywords

Michael addition
asymmetric catalysis
bis(thiazolines)
fluorination
pyrans
squaramides

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abstract = "An efficient highly diastereo- and enantioselective protocol to access optically pure fluorine-containing 2-amino-cyclopenta[b]pyran derivatives using Lewis acid catalysis and organocatalysis sequence has been developed. The corresponding products could be obtained in good to excellent yields with good to excellent diastereoselectivity and enantioselectivity (up to 99:1 dr, >99% ee).",

keywords = "Michael addition, asymmetric catalysis, bis(thiazolines), fluorination, pyrans, squaramides",

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AU - Zhao, Bo Liang

AU - Du, Da Ming

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N2 - An efficient highly diastereo- and enantioselective protocol to access optically pure fluorine-containing 2-amino-cyclopenta[b]pyran derivatives using Lewis acid catalysis and organocatalysis sequence has been developed. The corresponding products could be obtained in good to excellent yields with good to excellent diastereoselectivity and enantioselectivity (up to 99:1 dr, >99% ee).

AB - An efficient highly diastereo- and enantioselective protocol to access optically pure fluorine-containing 2-amino-cyclopenta[b]pyran derivatives using Lewis acid catalysis and organocatalysis sequence has been developed. The corresponding products could be obtained in good to excellent yields with good to excellent diastereoselectivity and enantioselectivity (up to 99:1 dr, >99% ee).

KW - Michael addition

KW - asymmetric catalysis

KW - bis(thiazolines)

KW - fluorination

KW - pyrans

KW - squaramides

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ER -

A Combination of Metal and Organic Catalysis: Highly Diastereo- and Enantioselective Construction of Fluorinated 2-Aminocyclopenta[b]pyran Derivatives

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Keywords

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