Recyclable organocatalyst-promoted one-pot Michael/aza-Henry/lactamization reactions for fluorinated 2-piperidinones bearing four stereogenic centres

Xin Huang; Kenny Pham; Xiaofeng Zhang; Wen Bin Yi; Jeremy H. Hyatt; Anthony P. Tran; Jerry P. Jasinski; Wei Zhang

doi:10.1039/c5ra15306a

Recyclable organocatalyst-promoted one-pot Michael/aza-Henry/lactamization reactions for fluorinated 2-piperidinones bearing four stereogenic centres

Xin Huang
, Kenny Pham
, Xiaofeng Zhang
, Wen Bin Yi
, Jeremy H. Hyatt
, Anthony P. Tran
, Jerry P. Jasinski
, Wei Zhang

Chemistry

University of Massachusetts Boston
Nanjing University of Science and Technology
Keene State College

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

Abstract

A one-pot Michael/aza-Henry/lactamization reaction promoted by recyclable fluorous bifunctional cinchona alkaloid/thiourea organocatalyst has been developed for asymmetric synthesis of fluorine-containing 2-piperidinones bearing four stereogenic centers. The asymmetric Michael adducts induce the formation of other three stereogenic centers to afford products with up to 99% ee and 15:1 dr.

Original language	English
Pages (from-to)	71071-71075
Number of pages	5
Journal	RSC Advances
Volume	5
Issue number	87
DOIs	https://doi.org/10.1039/c5ra15306a
State	Published - Aug 13 2015

ASJC Scopus Subject Areas

General Chemistry
General Chemical Engineering

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10.1039/c5ra15306a

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title = "Recyclable organocatalyst-promoted one-pot Michael/aza-Henry/lactamization reactions for fluorinated 2-piperidinones bearing four stereogenic centres",

abstract = "A one-pot Michael/aza-Henry/lactamization reaction promoted by recyclable fluorous bifunctional cinchona alkaloid/thiourea organocatalyst has been developed for asymmetric synthesis of fluorine-containing 2-piperidinones bearing four stereogenic centers. The asymmetric Michael adducts induce the formation of other three stereogenic centers to afford products with up to 99\% ee and 15:1 dr.",

author = "Xin Huang and Kenny Pham and Xiaofeng Zhang and Yi, \{Wen Bin\} and Hyatt, \{Jeremy H.\} and Tran, \{Anthony P.\} and Jasinski, \{Jerry P.\} and Wei Zhang",

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year = "2015",

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doi = "10.1039/c5ra15306a",

language = "English",

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T1 - Recyclable organocatalyst-promoted one-pot Michael/aza-Henry/lactamization reactions for fluorinated 2-piperidinones bearing four stereogenic centres

AU - Huang, Xin

AU - Pham, Kenny

AU - Zhang, Xiaofeng

AU - Yi, Wen Bin

AU - Hyatt, Jeremy H.

AU - Tran, Anthony P.

AU - Jasinski, Jerry P.

AU - Zhang, Wei

PY - 2015/8/13

Y1 - 2015/8/13

N2 - A one-pot Michael/aza-Henry/lactamization reaction promoted by recyclable fluorous bifunctional cinchona alkaloid/thiourea organocatalyst has been developed for asymmetric synthesis of fluorine-containing 2-piperidinones bearing four stereogenic centers. The asymmetric Michael adducts induce the formation of other three stereogenic centers to afford products with up to 99% ee and 15:1 dr.

AB - A one-pot Michael/aza-Henry/lactamization reaction promoted by recyclable fluorous bifunctional cinchona alkaloid/thiourea organocatalyst has been developed for asymmetric synthesis of fluorine-containing 2-piperidinones bearing four stereogenic centers. The asymmetric Michael adducts induce the formation of other three stereogenic centers to afford products with up to 99% ee and 15:1 dr.

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UR - https://www.scopus.com/pages/publications/84940551520#tab=citedBy

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DO - 10.1039/c5ra15306a

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JF - RSC Advances

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ER -

Recyclable organocatalyst-promoted one-pot Michael/aza-Henry/lactamization reactions for fluorinated 2-piperidinones bearing four stereogenic centres

Abstract

ASJC Scopus Subject Areas

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