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Diastereodifferentiating [2+2] photocycloaddition of chiral cyclohexenone carboxylates with cyclopentene by a microreactor

Paper ID Volume ID Publish Year Pages File Format Full-Text
27004 43993 2012 7 PDF Available
Title
Diastereodifferentiating [2+2] photocycloaddition of chiral cyclohexenone carboxylates with cyclopentene by a microreactor
Abstract

We performed diastereodifferentiating [2+2] photocycloaddition of chiral cyclohexenone (1) with cyclopentene using a special continuous microflow reactor equipped with UV-LED lamps for photoreaction, and compared the results to batch processing. Even at very high sample concentration, the high conversion was accomplished in this microreactor; however, the reaction under the same conditions did not proceed to completion in the batch. Furthermore, the highest diastereomeric excess (de) of photoproducts was achieved in this microreactor when aromatic compounds were added, which prevented the reaction from proceeding to completion in the batch due to their high absorption coefficients. This diastereoselective enhancement was due to superior light penetration in the microreactor.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Microreactor shows the moderate transmission even at a very high concentration. ► Microreactor can proceed the photoreaction even at a very high concentration. ► We achieved the highest de of this photoreaction using this microreactor.

Keywords
Photocycloaddition; Diastereodifferentiating; Microreactor; Cyclohexenone
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Diastereodifferentiating [2+2] photocycloaddition of chiral cyclohexenone carboxylates with cyclopentene by a microreactor
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 242, 15 August 2012, Pages 13–19
Authors
, , , , , ,
Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us