Enantioselective addition of diorganozincs to aldehydes catalyzed by β-amino alcohols

R. Noyori; S. Suga; K. Kawai; S. Okada; M. Kitamura; N. Oguni; M. Hayashi; T. Kaneko; Y. Matsuda

doi:10.1016/0022-328X(90)85212-H

Enantioselective addition of diorganozincs to aldehydes catalyzed by β-amino alcohols

R. Noyori, S. Suga, K. Kawai, S. Okada, M. Kitamura, N. Oguni, M. Hayashi, T. Kaneko, Y. Matsuda

Research output: Contribution to journal › Article › peer-review

217 Citations (Scopus)

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	https://doi.org/10.1016/0022-328X(90)85212-H
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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title = "Enantioselective addition of diorganozincs to aldehydes catalyzed by β-amino alcohols",

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.",

author = "R. Noyori and S. Suga and K. Kawai and S. Okada and M. Kitamura and N. Oguni and M. Hayashi and T. Kaneko and Y. Matsuda",

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doi = "10.1016/0022-328X(90)85212-H",

language = "English",

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T1 - Enantioselective addition of diorganozincs to aldehydes catalyzed by β-amino alcohols

AU - Noyori, R.

AU - Suga, S.

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.

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SN - 0022-328X

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Enantioselective addition of diorganozincs to aldehydes catalyzed by β-amino alcohols

Abstract

ASJC Scopus subject areas

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