Tetrahedron Letters, volume 35, issue 18, pages 2861-2864

X-ray crystallographic studies provide additional evidence that an enzyme-like binding pocket is crucial to the enantioselective dihydroxylation of olefins by OsO4—bis-cinchona alkaloid complexes

E J Corey ¹

Mark C. Noe ¹

Sepehr Sarshar ¹

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Department of Chemistry, Harvard University, Cambridge, Massachusetts, 02138 USA |

Publication type: Journal Article

Publication date: 1994-05-01

Elsevier

Journal: Tetrahedron Letters

scimago Q3

wos Q3

SJR: 0.323

CiteScore: 3.5

Impact factor: 1.5

ISSN: 00404039, 18733581

DOI: 10.1016/S0040-4039(00)76644-5

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

X-Ray crystallographic analysis on single crystals and 1H NMR studies in solution of various bis-cinchona alkaloid derivatives reveal a general preference for a conformation which possesses a U-shaped binding pocket with favorable dimensions for the inclusion of olefinic substrates and the acceleration of face selective dihydroxylation by a proximate pentacoordinate OsO4.

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Corey E. J., Noe M. C., Sarshar S. X-ray crystallographic studies provide additional evidence that an enzyme-like binding pocket is crucial to the enantioselective dihydroxylation of olefins by OsO4—bis-cinchona alkaloid complexes // Tetrahedron Letters. 1994. Vol. 35. No. 18. pp. 2861-2864.

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RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/S0040-4039(00)76644-5

UR - https://doi.org/10.1016/S0040-4039(00)76644-5

TI - X-ray crystallographic studies provide additional evidence that an enzyme-like binding pocket is crucial to the enantioselective dihydroxylation of olefins by OsO4—bis-cinchona alkaloid complexes

T2 - Tetrahedron Letters

AU - Corey, E J

AU - Noe, Mark C.

AU - Sarshar, Sepehr

PY - 1994

DA - 1994/05/01

PB - Elsevier

SP - 2861-2864

IS - 18

VL - 35

SN - 0040-4039

SN - 1873-3581

ER -

BibTex |

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@article{1994_Corey,

author = {E J Corey and Mark C. Noe and Sepehr Sarshar},

title = {X-ray crystallographic studies provide additional evidence that an enzyme-like binding pocket is crucial to the enantioselective dihydroxylation of olefins by OsO4—bis-cinchona alkaloid complexes},

journal = {Tetrahedron Letters},

year = {1994},

volume = {35},

publisher = {Elsevier},

month = {may},

url = {https://doi.org/10.1016/S0040-4039(00)76644-5},

number = {18},

pages = {2861--2864},

doi = {10.1016/S0040-4039(00)76644-5}

}

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Corey, E. J., et al. “X-ray crystallographic studies provide additional evidence that an enzyme-like binding pocket is crucial to the enantioselective dihydroxylation of olefins by OsO4—bis-cinchona alkaloid complexes.” Tetrahedron Letters, vol. 35, no. 18, May. 1994, pp. 2861-2864. https://doi.org/10.1016/S0040-4039(00)76644-5.

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Publisher

Elsevier

Journal

Tetrahedron Letters

scimago Q3

wos Q3

SJR

0.323

CiteScore

3.5

Impact factor

1.5

ISSN

00404039 (Print)

18733581 (Electronic)