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Chiral catalysts for the enantioselective addition of organometallic reagents to aldehydes

✍ Scribed by E.J Corey; Francis J Hannon


Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
284 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis


A mechanistic model for the enantioselective addition of diethylzinc to benzaldehyde with chiral tridentate lithium complexes as catalysts correctly predicts the observed direction of enantioselectivity which occurs at levels of 8595% ee.

A recent paper from these laboratories described two rationally designed and effective chiral catalysts for the enantioselective conjugate addition of organocopper reagents to a$-en0nes.l Thus, the lithium salt derived 7. This research was assisted financially by a grant from the National Science Foundation.


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Optically active amino thioacetate derivatives of (+l-norephedrine were found to act as effective catalysts for enantioselective addition of diethylzinc to aldehydes. This reaction provided optically active secondary alcohols with e.e. of up to >99%.

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High levels of enantioselectivity have been achieved in the diethylzinc addition to both aromatic and aliphatic aldehydes, employing readily available N-substituted-azetidinyl(diphenylmethyl)methanols as chiral catalysts.