Toward creation of a universal NMR database for the stereochemical assignment of acyclic compounds: The case of two contiguous propionate units

Organic Letters

Volumn 1, Issue 13, 1999, Pages 2177-2180

  Kobayashi, Yoshihisa ^a   Lee, Jinhwa ^a   Tezuka, Kenichi ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC HYDROCARBON; PROPIONIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; FACTUAL DATABASE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

DATABASES, FACTUAL; HYDROCARBONS, ACYCLIC; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PROPIONATES; STEREOISOMERISM;

EID: 0033619844     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9903786     Document Type: Article

References (21)

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15. 19F NMR of its (R)-Mosher ester. It is worthwhile adding that 4 diastereomers 4b, 4d, 4e, and 4h obtained stereospecifically in the second crotylboration were found to be optically pure.
16. For examples similar to the present case, see ref 3a.
17. Keck, G. E.; Abbott, D. E. Tetrahedron Lett. 1984, 25, 1883-1886.
18. For the case of 4a, although the stereoselectivity (4a:4b) could be improved up to 5:1, a significant amount of the linear product (3:2 regioselectivity) was also formed.
19. 13C chemical shifts of two acetonide methyl groups are known to be diagnostic in differentiating syn-and anti-1,3-diol acetonides: (a) Rychnovsky, S. D.: Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945-948.
20. (b) Evans, D. A.; Reiger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099-7100. In addition, NOE studies were conducted on the acetonides to confirm the stereochemical assignment at C.5 and C.7.
21. CS ChemNMR Pro version 1.0. Renate Buergin Schaller, Development Centre, Bergstrasse 114, Zurich, Switzerland, installed in CS ChemDraw Pro version 4.5, was used.