Abstract
Nucleophilic addition of dialkylzincs to aldehydes in hydrocarbon solvents is markedly accelerated by the presence of a catalytic amount of a β-dialkylamino alcohol. Use of certain sterically constrained chiral amino alcohols such as 3-exo-(dimethylamino)isoborneol or 1-t-butyl-2-piperidinoethanol effects highly enantioselective catalysis giving secondary alcohols in up to 99% ee. Dimethyl-, diethyl-, di-n-butyl-, and di-n-pentyl-zincs have been employed for the alkylation of substituted benzaldehydes and some olefinic or aliphatic aldehydes. Configurational correlation between the chiral auxiliary and alkylation products is discussed.
Original language | English |
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Pages (from-to) | 19-37 |
Number of pages | 19 |
Journal | Journal of Organometallic Chemistry |
Volume | 382 |
Issue number | 1-2 |
DOIs | |
Publication status | Published - Feb 6 1990 |
Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
- Materials Chemistry