Asymmetric Organocatalytic Synthesis of Highly Functionalized Spirocyclohexane 
Indandiones via a One-Pot Michael/Michael/Aldol Sequence

Blümel, Marcus; Chauhan, Pankaj; Vermeeren, Cornelia; Dreier, Angelika; Lehmann, Christian W.; Enders, Dieter

doi:10.1055/s-0035-1560072

Local TagsRelease HistoryDetailsSummary

Asymmetric Organocatalytic Synthesis of Highly Functionalized Spirocyclohexane Indandiones via a One-Pot Michael/Michael/Aldol Sequence

Blümel, M., Chauhan, P., Vermeeren, C., Dreier, A., Lehmann, C. W., & Enders, D. (2015). Asymmetric Organocatalytic Synthesis of Highly Functionalized Spirocyclohexane Indandiones via a One-Pot Michael/Michael/Aldol Sequence. Synthesis, 47(22), 3618-3628. doi:10.1055/s-0035-1560072.

Item is Released

show all hide all

Basic

show hide

Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0029-3033-C Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0029-3034-A

Genre: Journal Article

Files

show Files

Locators

show

Creators

show

hide

Creators:
Blümel, Marcus¹, Author
Chauhan, Pankaj¹, Author
Vermeeren, Cornelia¹, Author
Dreier, Angelika², Author
Lehmann, Christian W.², Author
Enders, Dieter¹, Author

Affiliations:
1Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany, ou_persistent22
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625

Content

show

hide

Free keywords: organocatalysis; one-pot reaction; squaramide; trifluoromethyl group; spirocycles

Abstract: The asymmetric organocatalytic one-pot Michael/Michael/ aldol reaction of trifluoromethyl-substituted 1,3-dicarbonyl compounds, nitroolefins, and 2-arylidene indandiones catalyzed sequentially by a cinchona-derived squaramide and DBU leads to spirocyclohexane-indan-1,3-diones bearing five adjacent stereogenic centers including a trifluoromethylated one in medium to very good yields and enantioselectivities, but generally in low to high diastereomeric ratios.

Details

show

hide

Language(s): eng - English

Dates: Submitted: 2015-07-24Accepted: 2015-07-27Published Online: 2015-08-14Date issued: 2015-11-17

Publication Status: Issued

Pages: 11

Publishing info: -

Table of Contents: -

Rev. Type: Peer

Identifiers: DOI: 10.1055/s-0035-1560072

Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show

hide

Title: Synthesis

Source Genre: Journal

Creator(s):

Affiliations:

Publ. Info: Stuttgart : Georg Thieme Verlag

Pages: - Volume / Issue: 47 (22) Sequence Number: - Start / End Page: 3618 - 3628 Identifier: ISSN: 0039-7881
CoNE: https://pure.mpg.de/cone/journals/resource/954925448757