Direct enantioselective synthesis of bicyclic Diels-Alder products

Henrik Sundén; Ramon Rios; Yongmei Xu; Lars Eriksson; Armando Córdova

doi:10.1002/adsc.200700175

Direct enantioselective synthesis of bicyclic Diels-Alder products

Henrik Sundén
, Ramon Rios
, Yongmei Xu
, Lars Eriksson
, Armando Córdova

Chemistry

Arrhenius Laboratory

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

58 Scopus citations

Abstract

The direct amine-catalyzed enantioselective Diels-Alder reaction between α,β-unsaturated cyclic ketones and nitroolefins is presented. A simple diamine catalyzes the asymmetric Diels-Alder reaction with high stereoselectivity and furnishes the corresponding Diels-Alder adducts in good to high yields with >25:1 dr and up to 86% ee. The study demonstrates a convenient entry to functionalized bicyclic molecules contaning four stereocenters that are formed with excellent diastreoselectivity and good to high enantioselectivity.

Original language	British English
Pages (from-to)	2549-2555
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	349
Issue number	17-18
DOIs	https://doi.org/10.1002/adsc.200700175
State	Published - Dec 2007

Keywords

α,β-unsaturated cyclic ketones
Asymmetric catalysis
Diels-Alder reaction
Nitroolefins
Organocatalysis

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10.1002/adsc.200700175

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abstract = "The direct amine-catalyzed enantioselective Diels-Alder reaction between α,β-unsaturated cyclic ketones and nitroolefins is presented. A simple diamine catalyzes the asymmetric Diels-Alder reaction with high stereoselectivity and furnishes the corresponding Diels-Alder adducts in good to high yields with >25:1 dr and up to 86\% ee. The study demonstrates a convenient entry to functionalized bicyclic molecules contaning four stereocenters that are formed with excellent diastreoselectivity and good to high enantioselectivity.",

keywords = "α,β-unsaturated cyclic ketones, Asymmetric catalysis, Diels-Alder reaction, Nitroolefins, Organocatalysis",

author = "Henrik Sund{\'e}n and Ramon Rios and Yongmei Xu and Lars Eriksson and Armando C{\'o}rdova",

year = "2007",

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language = "British English",

volume = "349",

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T1 - Direct enantioselective synthesis of bicyclic Diels-Alder products

AU - Sundén, Henrik

AU - Rios, Ramon

AU - Xu, Yongmei

AU - Eriksson, Lars

AU - Córdova, Armando

PY - 2007/12

Y1 - 2007/12

N2 - The direct amine-catalyzed enantioselective Diels-Alder reaction between α,β-unsaturated cyclic ketones and nitroolefins is presented. A simple diamine catalyzes the asymmetric Diels-Alder reaction with high stereoselectivity and furnishes the corresponding Diels-Alder adducts in good to high yields with >25:1 dr and up to 86% ee. The study demonstrates a convenient entry to functionalized bicyclic molecules contaning four stereocenters that are formed with excellent diastreoselectivity and good to high enantioselectivity.

AB - The direct amine-catalyzed enantioselective Diels-Alder reaction between α,β-unsaturated cyclic ketones and nitroolefins is presented. A simple diamine catalyzes the asymmetric Diels-Alder reaction with high stereoselectivity and furnishes the corresponding Diels-Alder adducts in good to high yields with >25:1 dr and up to 86% ee. The study demonstrates a convenient entry to functionalized bicyclic molecules contaning four stereocenters that are formed with excellent diastreoselectivity and good to high enantioselectivity.

KW - α,β-unsaturated cyclic ketones

KW - Asymmetric catalysis

KW - Diels-Alder reaction

KW - Nitroolefins

KW - Organocatalysis

UR - https://www.scopus.com/pages/publications/37349125225

U2 - 10.1002/adsc.200700175

DO - 10.1002/adsc.200700175

M3 - Article

AN - SCOPUS:37349125225

SN - 1615-4150

VL - 349

SP - 2549

EP - 2555

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 17-18

ER -

Direct enantioselective synthesis of bicyclic Diels-Alder products

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Keywords

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