A Sequential Route to Cyclopentenes from 1,6‐Enynes and Diazo Ketones through Gold and Rhodium Catalysis

This work reports the construction of cyclopentene cores from 1,6‐enynes and aryl diazo ketones through two new reaction sequences involving initial gold‐catalyzed cyclization of 1,6‐enynes with diazo species, followed by rhodium‐catalyzed skeletal rearrangement of the resulting 3‐cyclopropyl‐2‐en‐1...

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Bibliographic Details
Published in:	Advanced synthesis & catalysis Vol. 359; no. 3; pp. 402 - 409
Main Authors:	Kale, Balaji S., Lee, Hsin‐Fu, Liu, Rai‐Shung
Format:	Journal Article
Language:	English
Published:	Heidelberg Wiley Subscription Services, Inc 02-02-2017
Subjects:	1,6-enynes Aromatic compounds Catalysis Chemical reactions Cyclopentene cyclopropylgold carbenes Derivatives diazo ketones formal [2+2+1]-cycloaddition Gold Ketones Organic compounds Phenyls Rhodium rhodium-catalyzed process
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Summary:	This work reports the construction of cyclopentene cores from 1,6‐enynes and aryl diazo ketones through two new reaction sequences involving initial gold‐catalyzed cyclization of 1,6‐enynes with diazo species, followed by rhodium‐catalyzed skeletal rearrangement of the resulting 3‐cyclopropyl‐2‐en‐1‐ones. In most instances the rhodium‐catalyzed reactions afforded cyclopentene derivatives whereas several n‐alkyl‐ or ortho‐substituted phenyl ketones delivered seven‐membered oxacycles. A plausible mechanism provides rationales for these two distinct products.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1615-4150 1615-4169
DOI:	10.1002/adsc.201600980