DOI: 10.1246/bcsj.68.36. Stereoselective Organic Synthesis via Dynamic Kinetic Resolution

Stereoselective Organic Synthesis via Dynamic Kinetic Resolution

10.1246/bcsj.68.36

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract Asymmetric catalysts, either chemical or biological, effect the reactions of enantiomeric substrates at unequal rates, allowing for the kinetic resolution of racemates. The asymmetric reaction of chirally labile compounds capable of undergoing in situ racemization can, in principle, afford a single stereoisomer in 100% ee and in 100% yield. The second-order reaction provides a powerful tool for the stereoselective synthesis of chiral compounds, as exemplified by, among others, the biochemical hydrolysis of hydantoins or oxazolinones and microbial reductions or BINAP–Ru(II) catalyzed hydrogenation of certain α-substituted β-keto esters. Such transformations are characterized by the presence of parallel reactions interrelated by the stereoinversion of the enantiomeric substrates. The efficiency is decisively affected by the kinetic parameters, particularly the relative rates of the stereoinversion and reaction as well as the intrinsic stereochemical parameters of the catalyst and substrate. Such stereoselective reactions via dynamic kinetic resolution are expressed mathematically and the stereochemical profiles are displayed graphically. The validity of this basic approach has been verified by the correlation to the experimental results.

Bibliography

Noyori, R., Tokunaga, M., & Kitamura, M. (1995). Stereoselective Organic Synthesis via Dynamic Kinetic Resolution. Bulletin of the Chemical Society of Japan, 68(1), 36â55.

Authors 3

Ryoji Noyori (first)
Makoto Tokunaga (additional)
Masato Kitamura (additional)

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Dates

Type	When
Created	19 years, 1 month ago (July 1, 2006, 1:48 a.m.)
Deposited	1 year, 7 months ago (Jan. 20, 2024, 5:26 a.m.)
Indexed	3 weeks ago (Aug. 7, 2025, 4:55 a.m.)
Issued	30 years, 7 months ago (Jan. 1, 1995)
Published	30 years, 7 months ago (Jan. 1, 1995)
Published Online	19 years, 1 month ago (June 30, 2006)
Published Print	30 years, 7 months ago (Jan. 1, 1995)

Funders 0

None

BibTeX

@article{Noyori_1995, title={Stereoselective Organic Synthesis via Dynamic Kinetic Resolution}, volume={68}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.68.36}, DOI={10.1246/bcsj.68.36}, number={1}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Noyori, Ryoji and Tokunaga, Makoto and Kitamura, Masato}, year={1995}, month=jan, pages={36–55} }

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