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Synfacts 2018; 14(06): 0593
DOI: 10.1055/s-0037-1609763
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Iridium-Catalyzed Alkylation of Allenylic Electrophiles

Contributor(s):
Mark Lautens
,
Nicolas Zeidan
Petrone DA. Isomura M. Franzoni I. Rössler SL. Carreira EM. * ETH Zürich, Switzerland and University of Toronto, Canada
Allenylic Carbonates in Enantioselective Iridium-Catalyzed Alkylations.

J. Am. Chem. Soc. 2018;
140: 4697-4704
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Further Information

Publication History

Publication Date:
17 May 2018 (online)

 
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Key words

iridium catalysis - alkylation - allenes

Significance

Carreira and co-workers have reported an iridium-catalyzed enantioselective alkylation using allenylic carbonates as electrophiles. Chiral allenes are isolated in good yields, with excellent regio- and stereoselectivity.


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Comment

The products are further derivatized, providing examples of useful chiral building blocks. Mechanistic studies suggest that the catalyst has no kinetic preference for a specific substrate enantiomer and that the enantioselectivity is strictly under catalyst control.


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