Synthesis of gem-difluoromethylenated analogues of boronolide

The straightforward synthesis of four gem-difluoromethylenated analogues 4–7 of boronolide is described. The key steps of the synthesis include the concise preparation of the key intermediates 12a–b through the indium-mediated gem-difluoropropargylation of aldehyde 9 with the fluorine-containing bui...

Full description

Bibliographic Details
Main Authors:	Jing Lin, Xiao-Long Qiu, Feng-Ling Qing
Format:	Article
Language:	English
Published:	Beilstein-Institut 2010-04-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	boronolide gem-difluoromethylenated analogues gem-difluoropropargylation α,β-unsaturated-δ-lactones
Online Access:	https://doi.org/10.3762/bjoc.6.37

id	doaj-c2d9dd36904248c39a2c63b0a61543c5
record_format	Article
spelling	doaj-c2d9dd36904248c39a2c63b0a61543c52021-02-02T01:53:31ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972010-04-01613710.3762/bjoc.6.371860-5397-6-37Synthesis of gem-difluoromethylenated analogues of boronolideJing Lin0Xiao-Long Qiu1Feng-Ling Qing2College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, ChinaKey Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, ChinaCollege of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, ChinaThe straightforward synthesis of four gem-difluoromethylenated analogues 4–7 of boronolide is described. The key steps of the synthesis include the concise preparation of the key intermediates 12a–b through the indium-mediated gem-difluoropropargylation of aldehyde 9 with the fluorine-containing building block 11 and the efficient construction of α,β-unsaturated-δ-lactones 15a–b via BAIB/TEMPO-procedure.https://doi.org/10.3762/bjoc.6.37boronolidegem-difluoromethylenated analoguesgem-difluoropropargylationα,β-unsaturated-δ-lactones
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Jing Lin Xiao-Long Qiu Feng-Ling Qing
spellingShingle	Jing Lin Xiao-Long Qiu Feng-Ling Qing Synthesis of gem-difluoromethylenated analogues of boronolide Beilstein Journal of Organic Chemistry boronolide gem-difluoromethylenated analogues gem-difluoropropargylation α,β-unsaturated-δ-lactones
author_facet	Jing Lin Xiao-Long Qiu Feng-Ling Qing
author_sort	Jing Lin
title	Synthesis of gem-difluoromethylenated analogues of boronolide
title_short	Synthesis of gem-difluoromethylenated analogues of boronolide
title_full	Synthesis of gem-difluoromethylenated analogues of boronolide
title_fullStr	Synthesis of gem-difluoromethylenated analogues of boronolide
title_full_unstemmed	Synthesis of gem-difluoromethylenated analogues of boronolide
title_sort	synthesis of gem-difluoromethylenated analogues of boronolide
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2010-04-01
description	The straightforward synthesis of four gem-difluoromethylenated analogues 4–7 of boronolide is described. The key steps of the synthesis include the concise preparation of the key intermediates 12a–b through the indium-mediated gem-difluoropropargylation of aldehyde 9 with the fluorine-containing building block 11 and the efficient construction of α,β-unsaturated-δ-lactones 15a–b via BAIB/TEMPO-procedure.
topic	boronolide gem-difluoromethylenated analogues gem-difluoropropargylation α,β-unsaturated-δ-lactones
url	https://doi.org/10.3762/bjoc.6.37
work_keys_str_mv	AT jinglin synthesisofgemdifluoromethylenatedanaloguesofboronolide AT xiaolongqiu synthesisofgemdifluoromethylenatedanaloguesofboronolide AT fenglingqing synthesisofgemdifluoromethylenatedanaloguesofboronolide
_version_	1724310890086400000

Synthesis of gem-difluoromethylenated analogues of boronolide

Similar Items