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 |
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ASJC Scopus subject areas
- Biochemistry
- Chemical Engineering (miscellaneous)
- Inorganic Chemistry
- Organic Chemistry
- Physical and Theoretical Chemistry
- Materials Science (miscellaneous)
- Materials Chemistry
Cite this
Enantioselective addition of diorganozincs to aldehydes catalyzed by β-amino alcohols. / Noyori, R.; Suga, Seiji; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y.
In: Journal of Organometallic Chemistry, Vol. 382, No. 1-2, 06.02.1990, p. 19-37.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Enantioselective addition of diorganozincs to aldehydes catalyzed by β-amino alcohols
AU - Noyori, R.
AU - Suga, Seiji
AU - Kawai, K.
AU - Okada, S.
AU - Kitamura, M.
AU - Oguni, N.
AU - Hayashi, M.
AU - Kaneko, T.
AU - Matsuda, Y.
PY - 1990/2/6
Y1 - 1990/2/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0002904790&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0002904790&partnerID=8YFLogxK
U2 - 10.1016/0022-328X(90)85212-H
DO - 10.1016/0022-328X(90)85212-H
M3 - Article
AN - SCOPUS:0002904790
VL - 382
SP - 19
EP - 37
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
SN - 0022-328X
IS - 1-2
ER -