Asymmetric synthesis of pyrimidyl alkanol without adding chiral substances by the addition of diisopropylzinc to pyrimidine-5-carbaldehyde in conjunction with asymmetric autocatalysis

Kenso Soai; Itaru Sato; Takanori Shibata; Soichiro Komiya; Masanobu Hayashi; Yohei Matsueda; Hikaru Imamura; Tadakatsu Hayase; Hiroshi Morioka; Hayami Tabira; Jun Yamamoto; Yasunori Kowata

doi:10.1016/S0957-4166(02)00791-7

Asymmetric synthesis of pyrimidyl alkanol without adding chiral substances by the addition of diisopropylzinc to pyrimidine-5-carbaldehyde in conjunction with asymmetric autocatalysis

Kenso Soai^*, Itaru Sato, Takanori Shibata, Soichiro Komiya, Masanobu Hayashi, Yohei Matsueda, Hikaru Imamura, Tadakatsu Hayase, Hiroshi Morioka, Hayami Tabira, Jun Yamamoto, Yasunori Kowata

^*Corresponding author for this work

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

215 Citations (Scopus)

Abstract

Enantiomerically enriched pyrimidyl alkanol with either S or R configuration was obtained stochastically from the reaction between pyrimidine-5-carbaldehyde and diisopropylzinc without adding chiral substances in conjunction with subsequent asymmetric autocatalysis, leading to amplification of the enantiomeric excess.

Original language	English
Pages (from-to)	185-188
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	14
Issue number	2
DOIs	https://doi.org/10.1016/S0957-4166(02)00791-7
Publication status	Published - 2003 Jan 17
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/S0957-4166(02)00791-7

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Soai, K., Sato, I., Shibata, T., Komiya, S., Hayashi, M., Matsueda, Y., Imamura, H., Hayase, T., Morioka, H., Tabira, H., Yamamoto, J., & Kowata, Y. (2003). Asymmetric synthesis of pyrimidyl alkanol without adding chiral substances by the addition of diisopropylzinc to pyrimidine-5-carbaldehyde in conjunction with asymmetric autocatalysis. Tetrahedron Asymmetry, 14(2), 185-188. https://doi.org/10.1016/S0957-4166(02)00791-7

Asymmetric synthesis of pyrimidyl alkanol without adding chiral substances by the addition of diisopropylzinc to pyrimidine-5-carbaldehyde in conjunction with asymmetric autocatalysis. / Soai, Kenso; Sato, Itaru; Shibata, Takanori et al.
In: Tetrahedron Asymmetry, Vol. 14, No. 2, 17.01.2003, p. 185-188.

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

Soai, K, Sato, I, Shibata, T, Komiya, S, Hayashi, M, Matsueda, Y, Imamura, H, Hayase, T, Morioka, H, Tabira, H, Yamamoto, J & Kowata, Y 2003, 'Asymmetric synthesis of pyrimidyl alkanol without adding chiral substances by the addition of diisopropylzinc to pyrimidine-5-carbaldehyde in conjunction with asymmetric autocatalysis', Tetrahedron Asymmetry, vol. 14, no. 2, pp. 185-188. https://doi.org/10.1016/S0957-4166(02)00791-7

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abstract = "Enantiomerically enriched pyrimidyl alkanol with either S or R configuration was obtained stochastically from the reaction between pyrimidine-5-carbaldehyde and diisopropylzinc without adding chiral substances in conjunction with subsequent asymmetric autocatalysis, leading to amplification of the enantiomeric excess.",

author = "Kenso Soai and Itaru Sato and Takanori Shibata and Soichiro Komiya and Masanobu Hayashi and Yohei Matsueda and Hikaru Imamura and Tadakatsu Hayase and Hiroshi Morioka and Hayami Tabira and Jun Yamamoto and Yasunori Kowata",

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AU - Soai, Kenso

AU - Sato, Itaru

AU - Shibata, Takanori

AU - Komiya, Soichiro

AU - Hayashi, Masanobu

AU - Matsueda, Yohei

AU - Imamura, Hikaru

AU - Hayase, Tadakatsu

AU - Morioka, Hiroshi

AU - Tabira, Hayami

AU - Yamamoto, Jun

AU - Kowata, Yasunori

PY - 2003/1/17

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N2 - Enantiomerically enriched pyrimidyl alkanol with either S or R configuration was obtained stochastically from the reaction between pyrimidine-5-carbaldehyde and diisopropylzinc without adding chiral substances in conjunction with subsequent asymmetric autocatalysis, leading to amplification of the enantiomeric excess.

AB - Enantiomerically enriched pyrimidyl alkanol with either S or R configuration was obtained stochastically from the reaction between pyrimidine-5-carbaldehyde and diisopropylzinc without adding chiral substances in conjunction with subsequent asymmetric autocatalysis, leading to amplification of the enantiomeric excess.

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Asymmetric synthesis of pyrimidyl alkanol without adding chiral substances by the addition of diisopropylzinc to pyrimidine-5-carbaldehyde in conjunction with asymmetric autocatalysis

Abstract

ASJC Scopus subject areas

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