TY - JOUR
T1 - Contiguously substituted cyclooctane polyols. Configurational assignments via 1H NMR correlations and symmetry considerations
AU - Moura-Letts, Gustavo
AU - Paquette, Leo A.
PY - 2008/10/3
Y1 - 2008/10/3
N2 - (Chemical Equation Presented) More advanced oxidation of the cyclooctadienol shown, readily available in enantiomerically pure form from D-glucose, has given rise to a series of intermediates whose relative (and ultimately absolute) configuration was assigned on the basis of 1H/1H coupling constant analysis. The selectivities that were deduced in this manner were drawn from the sequential application of CrO3 oxidation in tandem with Luche reduction, two-step NMO-promoted osmylations bracketed by acetonide formation, and wholesale deprotection. The stereoselectivities of these reactions were traced by 1H NMR spectroscopy, and the stereochemical assignments were confirmed by the presence or absence of symmetry in the final cyclooctane polyols (four shown) generated in this investigation.
AB - (Chemical Equation Presented) More advanced oxidation of the cyclooctadienol shown, readily available in enantiomerically pure form from D-glucose, has given rise to a series of intermediates whose relative (and ultimately absolute) configuration was assigned on the basis of 1H/1H coupling constant analysis. The selectivities that were deduced in this manner were drawn from the sequential application of CrO3 oxidation in tandem with Luche reduction, two-step NMO-promoted osmylations bracketed by acetonide formation, and wholesale deprotection. The stereoselectivities of these reactions were traced by 1H NMR spectroscopy, and the stereochemical assignments were confirmed by the presence or absence of symmetry in the final cyclooctane polyols (four shown) generated in this investigation.
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U2 - 10.1021/jo801443d
DO - 10.1021/jo801443d
M3 - Article
C2 - 18761439
AN - SCOPUS:53049099090
VL - 73
SP - 7663
EP - 7670
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 19
ER -