TMSOTf-Promoted Addition of Alkynes to Aldehydes: A Novel Synthesis of Chroman-4-ones

Authors
Park, Ji YeonUllapu, Punna ReddyChoo, HyunahLee, Jae KyunMin, Sun-JoonPae, Ae NimKim, YouseungBaek, Du-JongCho, Yong Seo
Issue Date
2008-11
Publisher
WILEY-V C H VERLAG GMBH
Citation
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v.2008, no.32, pp.5461 - 5469
Abstract
A novel synthetic method to prepare chalcones 2 and chroman-4-ones 3 by TMSOTf-promoted addition of alkynes 1 to various aldehydes has been developed. The ratios of chalcones 2, chroman-4-ones 3 and hydrated products 4 varied depending upon the substituents R (nBu, phenyl, H and TMS) on the alkynes 1. We also describe the transformation of the chalcones 2 to the corresponding chroman-4-ones 3 under basic conditions. ( (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
Keywords
COUPLING REACTION; ASYMMETRIC-SYNTHESIS; FLAVANONES; HYDRATION; CHROMANONES; ACID; COUPLING REACTION; ASYMMETRIC-SYNTHESIS; FLAVANONES; HYDRATION; CHROMANONES; ACID; Addition; Aldehydes; Alkynes; Chromanone
ISSN
1434-193X
URI
https://pubs.kist.re.kr/handle/201004/133016
DOI
10.1002/ejoc.200800782
Appears in Collections:
KIST Article > 2008
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