One-pot organocatalytic domino Michael/α-alkylation reactions: highly enantioselective synthesis of functionalized cyclopentanones and cyclopentanols

Ramon Rios; Jan Vesely; Henrik Sundén; Ismail Ibrahem; Gui Ling Zhao; Armando Córdova

doi:10.1016/j.tetlet.2007.06.070

One-pot organocatalytic domino Michael/α-alkylation reactions: highly enantioselective synthesis of functionalized cyclopentanones and cyclopentanols

Ramon Rios
, Jan Vesely
, Henrik Sundén
, Ismail Ibrahem
, Gui Ling Zhao
, Armando Córdova

Chemistry

Arrhenius Laboratory

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

75 Scopus citations

Abstract

A simple, highly enantioselective catalytic route to cyclopentanones is presented. The chiral amine catalyzed domino Michael/α-alkylation reaction gives access to functionalized cyclopentanones in good to high yields with 93 → 99% ee. The products were also reduced with high diastereoselectivity to the corresponding cyclopentanols.

Original language	British English
Pages (from-to)	5835-5839
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2007.06.070
State	Published - 13 Aug 2007

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title = "One-pot organocatalytic domino Michael/α-alkylation reactions: highly enantioselective synthesis of functionalized cyclopentanones and cyclopentanols",

abstract = "A simple, highly enantioselective catalytic route to cyclopentanones is presented. The chiral amine catalyzed domino Michael/α-alkylation reaction gives access to functionalized cyclopentanones in good to high yields with 93 → 99\% ee. The products were also reduced with high diastereoselectivity to the corresponding cyclopentanols.",

author = "Ramon Rios and Jan Vesely and Henrik Sund{\'e}n and Ismail Ibrahem and Zhao, \{Gui Ling\} and Armando C{\'o}rdova",

note = "Funding Information: We gratefully acknowledge the Swedish National Research Council and Carl-Trygger Foundation for financial support.",

year = "2007",

month = aug,

day = "13",

doi = "10.1016/j.tetlet.2007.06.070",

language = "British English",

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T1 - One-pot organocatalytic domino Michael/α-alkylation reactions

T2 - highly enantioselective synthesis of functionalized cyclopentanones and cyclopentanols

AU - Rios, Ramon

AU - Vesely, Jan

AU - Sundén, Henrik

AU - Ibrahem, Ismail

AU - Zhao, Gui Ling

AU - Córdova, Armando

N1 - Funding Information: We gratefully acknowledge the Swedish National Research Council and Carl-Trygger Foundation for financial support.

PY - 2007/8/13

Y1 - 2007/8/13

N2 - A simple, highly enantioselective catalytic route to cyclopentanones is presented. The chiral amine catalyzed domino Michael/α-alkylation reaction gives access to functionalized cyclopentanones in good to high yields with 93 → 99% ee. The products were also reduced with high diastereoselectivity to the corresponding cyclopentanols.

AB - A simple, highly enantioselective catalytic route to cyclopentanones is presented. The chiral amine catalyzed domino Michael/α-alkylation reaction gives access to functionalized cyclopentanones in good to high yields with 93 → 99% ee. The products were also reduced with high diastereoselectivity to the corresponding cyclopentanols.

UR - https://www.scopus.com/pages/publications/34447511093

U2 - 10.1016/j.tetlet.2007.06.070

DO - 10.1016/j.tetlet.2007.06.070

M3 - Article

AN - SCOPUS:34447511093

SN - 0040-4039

VL - 48

SP - 5835

EP - 5839

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

One-pot organocatalytic domino Michael/α-alkylation reactions: highly enantioselective synthesis of functionalized cyclopentanones and cyclopentanols

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