A domino aldol addition/hemiketal formation/hemiketal formation/epimerization route to a heteroadamantane. A crystal-structure, NMR, and computational study
Glaser H, Puchta R, van Eikema Hommes N, Leusser D, Murso A, Stalke D, Bauer W, Saalfrank R (2002)
Publication Status: Published
Publication Type: Journal article
Publication year: 2002
Journal
Publisher: Wiley-Blackwell
Book Volume: 85
Pages Range: 3828-3841
Journal Issue: 11
DOI: 10.1002/1522-2675(200211)85:11<3828::AID-HLCA3828>3.0.CO;2-Z
Abstract
It has been found by serendipity during the attempted synthesis of the potential tris-bidentate ligand 7 that this compound undergoes multiple ring-closure reactions to form the heterodamantane derivative 12. This reaction involves a domino aldol addition/hemiketal formation/hemiketal formation/epimerization sequence. Compound 12 was studied intensively by X-ray crystal-structure analysis, NMR, and AM1 computations. Complete assignment of all H-1- and C-13-NMR signals was achieved by a combination of HMQC, HMBC, DPFGSE-NOE, COSY, and long-range-COSY experiments. The NMR data agreed well with the crystallographic and computational results. Accordingly, 12 is present as the thermodynamically most-stable diastereoisomer with relative u-configuration at centers C(8) and C(9). In summary, five stereogenic centers were created starting from an achiral precursor in an efficient cascade reaction under thermodynamic control.
Authors with CRIS profile
Ralph Puchta
Naturwissenschaftliche Fakultät
Nicolaas van Eikema Hommes
Computer-Chemie-Centrum
Walter Bauer
Lehrstuhl für Organische Chemie II
Rolf Saalfrank
Naturwissenschaftliche Fakultät
Involved external institutions
Germany (DE)How to cite
APA:
Glaser, H., Puchta, R., van Eikema Hommes, N., Leusser, D., Murso, A., Stalke, D.,... Saalfrank, R. (2002). A domino aldol addition/hemiketal formation/hemiketal formation/epimerization route to a heteroadamantane. A crystal-structure, NMR, and computational study. Helvetica Chimica Acta, 85(11), 3828-3841. https://dx.doi.org/10.1002/1522-2675(200211)85:11<3828::AID-HLCA3828>3.0.CO;2-Z
MLA:
Glaser, Horst, et al. "A domino aldol addition/hemiketal formation/hemiketal formation/epimerization route to a heteroadamantane. A crystal-structure, NMR, and computational study." Helvetica Chimica Acta 85.11 (2002): 3828-3841.
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