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Synfacts 2015; 11(3): 0271
DOI: 10.1055/s-0034-1380095
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Asymmetric C–H Functionalization of Methyl Ethers

Contributor(s):
Mark Lautens
,
Charles C. J. Loh
Guptill DM, Davies HM. L * Emory University, Atlanta, USA
2,2,2-Trichloroethyl Aryldiazoacetates as Robust Reagents for the Enantioselective C–H Functionalization of Methyl Ethers.

J. Am. Chem. Soc. 2014;
136: 17718-17721
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Publication History

Publication Date:
16 February 2015 (online)

 
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Key words

rhodium - C–H functionalization - carbene insertion

Significance

The asymmetric site-selective functionalization of unactivated sp3 C–H bonds is one of the most challenging reactions to date. Davies and co-workers demonstrated in this article the utility of trichloroethyl aryldiazoacetates as excellent substrates in the Rh-catalyzed enantioselective functionalization of methyl ethers.


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Comment

A wide spectrum of methyl ethers can be functionalized with trichloroethyl aryldiazoacetates with moderate and good yields and excellent enantioselectivities. In all cases, regioselectivity of the carbene insertion is on the less hindered methyl moiety. When a chiral ether was utilized, different diastereomeric products could be selectively accessed using opposite enantiomers of the chiral catalyst (matched and mismatched).


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