DOI: 10.1126/science.260.5116.1918. Optically Active Carbon: Kinetic Resolution of C <sub>76</sub> by Asymmetric Osmylation

Optically Active Carbon: Kinetic Resolution of C 76 by Asymmetric Osmylation

10.1126/science.260.5116.1918

Crossref journal-article

American Association for the Advancement of Science (AAAS)

Science (221)

Abstract

The chiral fullerene C 76 was kinetically resolved by asymmetric osmylation providing an example of an optically active allotrope of a pure element. C 76 recovered from the treatment of racemic C 76 with OsO 4 and a chiral alkaloid ligand, showed a specific rotation [α] D of -4000° (> 97 percent enantiomeric excess) and a circular dichroism spectrum corresponding to the ultraviolet spectrum. Regenerated C 76 formed by reducing the asymmetrically osmylated C 76 with SnCl 2 was enriched in the opposite enantiomer. Analysis of the local curvature of the C 76 molecule indicated that OsO 4 should selectively add to 2 of the 30 types of bonds in C 76 . This regioselectivity was supported chromatographically and interpreted in terms of the kinetic resolution.

Bibliography

Hawkins, J. M., & Meyer, A. (1993). Optically Active Carbon: Kinetic Resolution of C 76 by Asymmetric Osmylation. Science, 260(5116), 1918â1920.

Authors 2

Joel M. Hawkins (first)
Axel Meyer (additional)

References 14 Referenced 120

COLT, J.R., AN ABINITIO STUDY OF THE C-76 FULLERENE ISOMERS, JOURNAL OF PHYSICAL CHEMISTRY 96: 10265 (1992). (10.1021/j100204a032) / JOURNAL OF PHYSICAL CHEMISTRY (1992)
DIEDERICH, F, BEYOND C-60 - THE HIGHER FULLERENES, ACCOUNTS OF CHEMICAL RESEARCH 25: 119 (1992). (10.1021/ar00015a004) / ACCOUNTS OF CHEMICAL RESEARCH (1992)
ETTI, R, NATURE 353: 149 (1991). (10.1038/353149a0) / NATURE (1991)
HADDON, R. C., ACCOUNTS OF CHEMICAL RESEARCH 21: 243 (1988). (10.1021/ar00150a005) / ACCOUNTS OF CHEMICAL RESEARCH (1988)
HAWKINS, J.M., OSMYLATION OF C-60 - PROOF AND CHARACTERIZATION OF THE SOCCER-BALL FRAMEWORK, ACCOUNTS OF CHEMICAL RESEARCH 25: 150 (1992). (10.1021/ar00015a008) / ACCOUNTS OF CHEMICAL RESEARCH (1992)
HAWKINS, J.M., 2D NUCLEAR-MAGNETIC-RESONANCE ANALYSIS OF OSMYLATED C60, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 113: 7770 (1991). (10.1021/ja00020a054) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (1991)
HAWKINS, J.M., REGIOCHEMISTRY OF THE BISOSMYLATION OF C-60 - ORTHO, META, AND PARA IN 3-DIMENSIONS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 114: 7954 (1992). (10.1021/ja00046a076) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (1992)
10.1126/science.252.5003.312
HAWKINS J.M. unpublished data.
MARTIN, V.S., KINETIC RESOLUTION OF RACEMIC ALLYLIC ALCOHOLS BY ENANTIOSELECTIVE EPOXIDATION - A ROUTE TO SUBSTANCES OF ABSOLUTE ENANTIOMERIC PURITY, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 103: 6237 (1981). (10.1021/ja00410a053) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (1981)
Meurer, K. P., Topics in Current Chemistry 127: 32 (1985). / Topics in Current Chemistry (1985)
Schoofs, A. R., Asymmetric Synthesis 1: CH3 (1983). / Asymmetric Synthesis (1983)
SHARPLESS, K.B., NEW LIGANDS DOUBLE THE SCOPE OF THE CATALYTIC ASYMMETRIC DIHYDROXYLATION OF OLEFINS, JOURNAL OF ORGANIC CHEMISTRY 56: 4585 (1991). (10.1021/jo00015a001) / JOURNAL OF ORGANIC CHEMISTRY (1991)
SHARPLESS, K.B., THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - A NEW LIGAND CLASS AND A PROCESS IMPROVEMENT, JOURNAL OF ORGANIC CHEMISTRY 57: 2768 (1992). (10.1021/jo00036a003) / JOURNAL OF ORGANIC CHEMISTRY (1992)

Dates

Type	When
Created	18 years, 10 months ago (Oct. 5, 2006, 7:05 p.m.)
Deposited	1 year, 7 months ago (Jan. 12, 2024, 5:50 p.m.)
Indexed	2 months, 1 week ago (June 26, 2025, 7:26 p.m.)
Issued	32 years, 2 months ago (June 25, 1993)
Published	32 years, 2 months ago (June 25, 1993)
Published Print	32 years, 2 months ago (June 25, 1993)

Funders 0

None

BibTeX

@article{Hawkins_1993, title={Optically Active Carbon: Kinetic Resolution of C 76 by Asymmetric Osmylation}, volume={260}, ISSN={1095-9203}, url={http://dx.doi.org/10.1126/science.260.5116.1918}, DOI={10.1126/science.260.5116.1918}, number={5116}, journal={Science}, publisher={American Association for the Advancement of Science (AAAS)}, author={Hawkins, Joel M. and Meyer, Axel}, year={1993}, month=jun, pages={1918–1920} }

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