Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis

Greschner W, Neumann B, Stammler H-G, Gröger H, Kuck D (2015)
Angewandte Chemie (International ed. in English) 54(46): 13764-13768.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
Inherently chiral acetophenones and benzaldehydes bearing the large, bowl-shaped framework of tribenzotriquinacene (TBTQ) were synthesized in enantiomerically pure form employing enzyme catalysis. Five-step sequences involving lipase CAL-B lead to the (M)-enantiomers, (+)-2-acetyl-TBTQ (M)-5 and (+)-2-formyl-TBTQ (M)-6, whereas use of lipase PS leads to the (P)-enantiomers, (-)-2-acetyl-TBTQ (P)-5 and (-)-2-formyl-TBTQ (P)-6, with at least 99 % ee in each case. The absolute configuration of these rigid 3D building blocks was determined by X-ray diffraction analysis of the ketones 5 and by comparison of their chiroptical properties with those of the aldehydes 6.
Erscheinungsjahr
Zeitschriftentitel
Angewandte Chemie (International ed. in English)
Band
54
Zeitschriftennummer
46
Seite
13764-13768
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Greschner W, Neumann B, Stammler H-G, Gröger H, Kuck D. Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis. Angewandte Chemie (International ed. in English). 2015;54(46):13764-13768.
Greschner, W., Neumann, B., Stammler, H. - G., Gröger, H., & Kuck, D. (2015). Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis. Angewandte Chemie (International ed. in English), 54(46), 13764-13768. doi:10.1002/anie.201506906
Greschner, W., Neumann, B., Stammler, H. - G., Gröger, H., and Kuck, D. (2015). Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis. Angewandte Chemie (International ed. in English) 54, 13764-13768.
Greschner, W., et al., 2015. Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis. Angewandte Chemie (International ed. in English), 54(46), p 13764-13768.
W. Greschner, et al., “Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis”, Angewandte Chemie (International ed. in English), vol. 54, 2015, pp. 13764-13768.
Greschner, W., Neumann, B., Stammler, H.-G., Gröger, H., Kuck, D.: Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis. Angewandte Chemie (International ed. in English). 54, 13764-13768 (2015).
Greschner, Wilko, Neumann, Beate, Stammler, Hans-Georg, Gröger, Harald, and Kuck, Dietmar. “Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis”. Angewandte Chemie (International ed. in English) 54.46 (2015): 13764-13768.

5 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Poly-Lewis-acids based on bowl-shaped tribenzotriquinacene.
Tomaschautzky J, Neumann B, Stammler HG, Mitzel NW., Dalton Trans 46(4), 2017
PMID: 28045169
Synthesis of Enantiopure C3 -Symmetric Triangular Molecules.
Miura T, Nakamuro T, Stewart SG, Nagata Y, Murakami M., Angew Chem Int Ed Engl 56(12), 2017
PMID: 28194832
Synthetically useful variants of industrial lipases from Burkholderia cepacia and Pseudomonas fluorescens.
Yoshida K, Ono M, Yamamoto T, Utsumi T, Koikeda S, Ema T., Org Biomol Chem 15(41), 2017
PMID: 28956057
Apical Functionalization of Tribenzotriquinacenes.
Dhara A, Weinmann J, Krause AM, Beuerle F., Chemistry 22(35), 2016
PMID: 27444414
Chirality-Assisted Synthesis of a Very Large Octameric Hydrogen-Bonded Capsule.
Beaudoin D, Rominger F, Mastalerz M., Angew Chem Int Ed Engl 55(50), 2016
PMID: 27862733

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