Preparation and separation of all possible rotamers of a stereochemical analog of meso-tartaric acid: Optically inactive and optically active isomers of (R,S)-2,2′-bis(methoxycarbonyl)-6,6′-dimethyl-9,9′- bitriptycyl

Tetrahedron

Volumn 58, Issue 52, 2002, Pages 10345-10351

  Toyota, Shinji ^a   Nakagawa, Takashi ^a   Kotani, Masashi ^a   Oki, Michinori ^a   Uekusa, Hidehiro ^b   Ohashi, Yuji ^b  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

CD; meso tartaric acid; Optical activity; Rotamer; Stereochemistry

Indexed keywords

2,2' BIS(METHOXYCARBONYL) 6,6' DIMETHYL 9,9' BITRIPTYCYL; CARBONYL DERIVATIVE; TARTARIC ACID; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHROMATOGRAPHY; CONFORMATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0037164660     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01408-4     Document Type: Article

References (10)

1. (a) Noller C.R. Science. 102:1945;508-509
2. The lack of meaning of internal compensation was proposed by the conformational considerations. The author mentioned the possibility of optical resolution by use of meso-tartaric acid type compounds. For the rebuttal to the Noller's proposal, see: (b) Wright G.F. Science. 104:1946;190-191.
3. Ōki M. The Chemistry of Rotational Isomers. 1993;Springer, Heidelberg.
4. Toyota S., Yasutomi A., Kojima H., Igarashi Y., Asakura M., Oki M. Bull. Chem. Soc. Jpn. 71:1998;2715-2720.
5. Schwarz L.H., Youkotus C., Kukakola P., Yu C.S. J. Org. Chem. 51:1986;995-999.
6. (a) Barnett E.D.B., Wiltshire J.L. J. Chem. Soc. 1928;1822-1825.
7. (b) Utz C.G., Chechter H. J. Org. Chem. 50:1985;5705-5709.
8. *)-1. We consider that the missing isomer should be kinetically unfavorable in the reaction of the intermediate product with a second molecule of benzyne, because we could not find it in any fractions in the chromatographic separation.
9. Landolt H. Das optische Drehungsvermögen organischer Substanzen. 1879;Vieweg und Sohn, Braunschweig. The classical explanation is that a molecule consisting of two asymmetric halves is optically inactive by 'internal compensation', because they should rotate the plane of polarization equal amounts in the opposite directions.
10. Prabhu V.S., Keana J.F.W. Org. Prep. Proced. Int. 16:1984;329-333.