Asymmetric synthesis of a chiral buckybowl, trimethylsumanene

Journal of the American Chemical Society

Volumn 130, Issue 27, 2008, Pages 8592-8593

  Higashibayashi, Shuhei ^a   Sakurai, Hidehiro ^a,b  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

8,13,18 TRIMETHYLSUMANENE; AROMATIC COMPOUND; CARBON;

AROMATIZATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; CHIRALITY; GEOMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LOW TEMPERATURE; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; STRUCTURE ANALYSIS;

EID: 46949085291     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja802822k     Document Type: Article

References (29)

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18. Expressions for the chirality of buckybowls and the stereodescriptor system for the configurations have not been officially established yet. We refer to the chirality as "bowl chirality" for convenience. The absolute configuration of bowl chirality of 1, 6, and 7 is shown by following two independent stereodescriptors. (a) (C) or (A) based on fullerene nomenclature; see ref 5a.
19. (b) (P) or (M) proposed in the following reference: Petrukhina, M.; Andreini, K. W.; Peng, L.; Scott, L. T. Angew. Chem., Int. Ed. 2004, 43, 5477-5481. (see the Supporting Information in detail)
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24. DFT calculation (B3LYP/6-311+G**) predicts inversion energy barriers of 19.3 and 18.3 kcal/mol for 1 and sumanene, respectively. Since the observed value for sumanene was reported to be 19.7-20.4 kcal/mol, the real value for 1 was estimated to be ca. 21 kcal/mol. For the observed value of 1, see the following reference: Amaya, T.; Sakane, H.; Muneishi, T.; Hirao, T. Chem. Commun. 2008, 76, 5-767.
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28. Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M. Synthesis 1981, 1001-1003.
29. Even the bowl-to-bowl inversion of (C)-(8R, 13R,18R)-6 gives the diastereomer (A)-(8R, 13R,18R)-6. Trimethylsilyl groups preferring the exo position freeze the bowl-to-bowl inversion as well (ref 2b).