DOI: 10.1246/cl.1977.429. ASYMMETRIC CROSS ALDOL SYNTHESIS. ASYMMETRIC ADDITION OF SILYL ENOL ETHER AND KETENE SILYL ACETAL TO α-KETO ESTERS

ASYMMETRIC CROSS ALDOL SYNTHESIS. ASYMMETRIC ADDITION OF SILYL ENOL ETHER AND KETENE SILYL ACETAL TO α-KETO ESTERS

10.1246/cl.1977.429

Crossref journal-article

Oxford University Press (OUP)

Chemistry Letters (286)

Abstract

Abstract Asymmetric cross aldol synthesis was carried out by the reaction of several silyl enol ethers and ketene silyl acetals with (−)-menthyl pyruvate and phenylglyoxylate. The extent of asymmetric induction realized in the reaction was determined to be in the range 18-68% by nmr using a shift reagent, Eu(fod)3, and was considerably larger than that observed in the reaction of the chiral α-keto esters with Grignard reagents.

Bibliography

Ojima, I., Yoshida, K., & Inaba, S. (1977). ASYMMETRIC CROSS ALDOL SYNTHESIS. ASYMMETRIC ADDITION OF SILYL ENOL ETHER AND KETENE SILYL ACETAL TO Î±-KETO ESTERS. Chemistry Letters, 6(4), 429â432.

Authors 3

Iwao Ojima (first)
Katsuhiko Yoshida (additional)
Shin-ichi Inaba (additional)

References 8 Referenced 19

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10.1021/ja00831a019
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10.1039/CT9068900365
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Dates

Type	When
Created	19 years, 1 month ago (July 24, 2006, 10:03 p.m.)
Deposited	1 year, 7 months ago (Jan. 19, 2024, 5:31 a.m.)
Indexed	1 year, 7 months ago (Jan. 19, 2024, 7:03 p.m.)
Issued	48 years, 5 months ago (April 1, 1977)
Published	48 years, 5 months ago (April 1, 1977)
Published Online	19 years, 5 months ago (March 27, 2006)
Published Print	48 years, 5 months ago (April 5, 1977)

Funders 0

None

BibTeX

@article{Ojima_1977, title={ASYMMETRIC CROSS ALDOL SYNTHESIS. ASYMMETRIC ADDITION OF SILYL ENOL ETHER AND KETENE SILYL ACETAL TO α-KETO ESTERS}, volume={6}, ISSN={1348-0715}, url={http://dx.doi.org/10.1246/cl.1977.429}, DOI={10.1246/cl.1977.429}, number={4}, journal={Chemistry Letters}, publisher={Oxford University Press (OUP)}, author={Ojima, Iwao and Yoshida, Katsuhiko and Inaba, Shin-ichi}, year={1977}, month=apr, pages={429–432} }

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