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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Abstract
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.
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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.
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.
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PMID: 26404021
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