Planar Chiral Imidazolium Salts in the Asymmetric Rhodium-Catalyzed 1,2-Addition of Arylboronic Acids to Aldehydes

Abstract

Planar chiral imidazolium salts 8 and 13 were used as precursors for N-heterocyclic carbene ligands, which were applied in rhodium-catalyzed additions of arylboronic acids to aromatic aldehydes. With pseudo-ortho-disubstituted [2.2]paracyclophane (S,R _p)-8b bearing a phosphinoyl substituent at the paracyclophane backbone, 38% ee has been achieved in this rather unexplored reaction.

[2.2]paracyclophane - N-heterocyclic carbene - imidazolium salt - asymmetric catalysis - boronic acid - diarylmethanol

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22

Without addition of TMEDA, the yields were up to 10% lower.

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24

Preliminary attempts to use rhodium catalysts bearing analogous planar chiral ligands obtained from oxazoline- or phosphine-containing imidazolium salts (cf. Ref. [17a] or Ref., [17b] respectively) revealed a low catalytic activity of those complexes.

25

With the same catalyst R-configured diarylmethanols can also be obtained. For example, starting from 1-naphthylboronic acid and benzaldehyde, use of (S,R _p)-7b afforded the (R)-3g with the same ee as stated in Table [2] .

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