DOI: 10.1246/bcsj.51.1183. Asymmetric Reactions. III. The Asymmetric Synthesis of Methyl 2-Phenylpropionate in the Presence of Chiral Polymers

Asymmetric Reactions. III. The Asymmetric Synthesis of Methyl 2-Phenylpropionate in the Presence of Chiral Polymers

10.1246/bcsj.51.1183

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract The asymmetric addition of methanol to phenylmethylketene was carried out in the presence of a chiral polymer obtained by the co-polymerization of N-benzyl-2-pyrrolidinylmethyl acrylate with methyl acrylate. The products obtained for the above co-polymer showed a correlation between logkR⁄kS and 1⁄T deviating from linearity, while those for poly(N-benzyl-2-pyrroIidinylmethyl acrylate) exhibited a linear relationship. N-Benzyl-2-pyrrolidinylmethyl butyrate, hexanoate, and stearate were also used as catalysts; they showed asymmetric efficiencies intermediate between those of N-benzyl-2-pyrrolidinylmethyl propionate and poly(N-benzyl-2-pyrrolidinylmethyl acrylate). The use of several high- and low-molecular-weight catalysts derived from cinchonine was similarly attempted in order to examine the polymer effect with regard to the stereoselectivity.

Bibliography

Yamashita, T., Yasueda, H., Nakatani, N., & Nakamura, N. (1978). Asymmetric Reactions. III. The Asymmetric Synthesis of Methyl 2-Phenylpropionate in the Presence of Chiral Polymers. Bulletin of the Chemical Society of Japan, 51(4), 1183â1185.

Authors 4

Tetsushi Yamashita (first)
Hiroshi Yasueda (additional)
Noriyuki Nakatani (additional)
Nobuo Nakamura (additional)

References 4 Referenced 20

Dates

Type	When
Created	19 years, 1 month ago (July 19, 2006, 11:06 p.m.)
Deposited	1 year, 7 months ago (Jan. 17, 2024, 5:11 a.m.)
Indexed	1 year, 7 months ago (Jan. 17, 2024, 7:02 p.m.)
Issued	47 years, 5 months ago (April 1, 1978)
Published	47 years, 5 months ago (April 1, 1978)
Published Online	19 years, 4 months ago (April 19, 2006)
Published Print	47 years, 5 months ago (April 1, 1978)

Funders 0

None

BibTeX

@article{Yamashita_1978, title={Asymmetric Reactions. III. The Asymmetric Synthesis of Methyl 2-Phenylpropionate in the Presence of Chiral Polymers}, volume={51}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.51.1183}, DOI={10.1246/bcsj.51.1183}, number={4}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Yamashita, Tetsushi and Yasueda, Hiroshi and Nakatani, Noriyuki and Nakamura, Nobuo}, year={1978}, month=apr, pages={1183–1185} }

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