NDLI: Catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols via direct aldol reaction of α-N3 amide

Content Provider	Royal Society of Chemistry (RSC)
Author	Amemiya, Fuyuki Noda, Hidetoshi Kumagai, Naoya Shibasaki, Masakatsu Weidner, Karin
Copyright Year	2017
Abstract	Organofluorine compounds are found in several important classes of chemicals, such as pharmaceuticals, agrochemicals, and functional materials. Chemists have been immensely interested in the development of methodologies for expeditious access to fluorine containing building blocks. In this study, we report a new method for the catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols with two contiguous stereogenic centers via the direct aldol reaction of an α-N3 amide to trifluoromethyl ketones. The key to the success of this method is the identification of a catalyst comprising Cu(II)/chiral hydroxamic acid to promote the desired aldol reaction, constructing a tetrasubstituted carbon in a highly stereoselective fashion. Despite substantial prior advances in asymmetric catalysis, this class of catalysts has not been utilized for the formation of carbon–carbon bond-forming reactions. Our mechanistic study sheds light on the unique profile of this catalytic system, where the Cu(II) complex plays a bifunctional role of serving as a Lewis acid and a Brønsted base. Furthermore, the densely functionalized aldol adducts undergo chemoselective transformations, affording a series of fluorine containing chiral building blocks with widespread application.
Starting Page	3260
Ending Page	3269
Page Count	10
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	8
Issue Number	4
Journal	Chemical Science
DOI	10.1039/c7sc00330g
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Stereoselectivity Fluorine Carboxylic acid Lewis Chirality Amide Aldol reaction Enantioselective synthesis Carbon
Content Type	Text
Resource Type	Article
Subject	Chemistry

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