An Unusual Pathway to Cyclobutane Formation via Desulfurative Intramolecular Photocycloaddition of an Enone Benzothiazoline Pair-Reference-Cited by-同舟云学术

An Unusual Pathway to Cyclobutane Formation via Desulfurative Intramolecular Photocycloaddition of an Enone Benzothiazoline Pair

Published:2009-03-20 Issue:8 Volume:11 Page:1685-1687
ISSN:1523-7060
Container-title:Organic Letters
language:en
Short-container-title:Org. Lett.

Author:

Jo Hyunil¹,Fitzgerald Mark E.¹,Winkler Jeffrey D.¹

Affiliation:

1. Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/ol900186y

Reference13 articles.

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4. The structure and stereochemistry of4were confirmed by X-ray crystallographic analysis of the corresponding sulfoxide26, which on chemical reduction (PBr3, CH2Cl2, 25 °C, 100% yield) gave4.The structure and stereochemistry of5were confirmed by X-ray crystallographic analysis of the corresponding N-acetylated product, which was obtained on irradiation of3(R = Ac).The N-acetylated photosubstrate3was prepared from amine7by acetylation and subsequent NaOMe-mediated cyclization.Experimental details and spectral data are included in theSupporting Information.

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