Concepedia

ENANTIOSELECTIVE ADDITION OF ACETYLENE TO ALDEHYDE. PREPARATION OF OPTICALLY ACTIVE ALKYNYL ALCOHOLS

Teruaki Mukaiyama, Keisuke Suzuki, Kenso Soai, Toshio Sato

Chemistry Letters · 1979 · 72 citations · 6 references

DOI

Concepts

Abstract

Abstract Enantioselective addition of acetylene to aldehyde was investigated by the use of (2S, 2′S)-2-hydroxymethyl-1-[(1-methylpyrrolidin-2-yl)methyl]pyrrolidine as a chiral ligand. The addition of lithium trimethylsilylacetylide to benzaldehyde afforded the corresponding alkynyl alcohol in 92% optical yield.

References

6

Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and .alpha.-methoxy-.alpha.-trifluoromethylphenylacetate (MTPA) esters

James A. Dale, Harry S. Mosher · Journal of the American Chemical Society · 1973 · 2.6K citations

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Synthetic studies on (2R,4'R,8'R)-.alpha.-tocopherol. Facile syntheses of optically active, saturated, acyclic isoprenoids via stereospecific [3,3] sigmatropic rearrangements

Ka-Kong Chan, Noal Cohen, James P. De Noble et al. · The Journal of Organic Chemistry · 1976 · 157 citations

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Total synthesis of prostaglandins. VII. Symmetric total synthesis of (-)-prostaglandin E1 and (-)-prostaglandin E2

Charles J. Sih, J. B. Heather, Rattan Sood et al. · Journal of the American Chemical Society · 1975 · 112 citations

, , +9

Asymmetric reduction. Reduction of acetylenic ketones with chiral hydride agent

R. S. Brinkmeyer, Vijaya M. Kapoor · Journal of the American Chemical Society · 1977 · 99 citations

, , +6

Synthesis and absolute configuration of (-)-methyl (E)-2,4,5-tetradecatrienoate, the sex attractant of the male dried bean weevil

William H. Pirkle, Charles W. Boeder · The Journal of Organic Chemistry · 1978 · 54 citations

, , +10