Abstract
The chromium-catalyzed enantioselective addition of carbo halides to carbonyl compounds is an important transformation in organic synthesis. However, the corresponding catalytic enantioselective arylation of ketones has not been reported to date. Herein, we report the first Cr-catalyzed enantioselective addition of aryl halides to both arylaliphatic and aliphatic ketones with high enantioselectivity in an intramolecular version, providing facile access to enantiopure tetrahydronaphthalen-1-ols and 2,3-dihydro-1H-inden-1-ols containing a tertiary alcohol.
Highlights
Catalytic enantioselective carbon–carbon bond formation reactions have achieved enormous development during the last few decades as a consequence of the growing demand for enantiopure compounds in modern industry, especially the pharmaceutical industry
The chromium (Cr)-catalyzed enantioselective addition of carbo halides to carbonyl compounds is one of the most reliable methods in organic chemistry for chemoselective and structurally diverse synthesis [1,2,3,4,5,6,7,8,9]
Since the first example of enantioselective allylation of aldehydes catalyzed by a Cr(II)–salen complex in 1999 by Cozzi and co-workers [12], several elegant catalytic enantioselective allylation and propargylation reactions have been developed by the groups of Nakada [13,14], Berkessel [15], Kishi [16], Sigman [17], Yamamoto [18], Guiry [19], Chen [20], Gade [21], White [22], and Zhang [23,24,25], respectively
Summary
Catalytic enantioselective carbon–carbon bond formation reactions have achieved enormous development during the last few decades as a consequence of the growing demand for enantiopure compounds in modern industry, especially the pharmaceutical industry. The chromium (Cr)-catalyzed enantioselective addition of carbo halides to carbonyl compounds is one of the most reliable methods in organic chemistry for chemoselective and structurally diverse synthesis [1,2,3,4,5,6,7,8,9]. The Cr-catalyzed enantioselective carbonyl addition reactions mainly focused on allylation, propargylation, alkenylation and alkylation of aldehydes [10,11]. The alkenylation and alkylation reactions were mainly explored by the Kishi group [26,27,28,29,30], and they established a toolbox approach to search for the specific ligand with a given substrate in the Cr-catalyzed process [28].
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