Planar chiral [2.2]paracyclophane-based phosphine-phenols: use in enantioselective [3 + 2] annulations of allenoates and N-tosylimines

Organic & Biomolecular Chemistry
Shinji KitagakiKeisuke Yoshida

Abstract

Planar chiral [2.2]paracyclophane-based phosphine-phenol catalysts, which have a benzene ring spacer inserted between the pseudo-ortho-substituted [2.2]paracyclophanol skeleton and the diarylphosphino group, are highly suitable for enantioselective [3 + 2] annulations of allenoates and N-tosylimines. These catalysts can be tuned by changing the substituent on the benzene rings of the diarylphosphino group. The observed enantioselectivity of 92% is the highest reported to date for phosphine-catalyzed annulations of unsubstituted allenic esters and N-tosylaldimines.

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Methods Mentioned

BETA
column chromatography
NMR

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