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 |
|---|---|
| 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
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Cite this
Noyori, R., Suga, S., Kawai, K., Okada, S., Kitamura, M., Oguni, N., Hayashi, M., Kaneko, T., & Matsuda, Y. (1990). Enantioselective addition of diorganozincs to aldehydes catalyzed by β-amino alcohols. Journal of Organometallic Chemistry, 382(1-2), 19-37. https://doi.org/10.1016/0022-328X(90)85212-H