Stereospecific diaza-Cope rearrangement as an efficient tool for the synthesis of DPEDA pyridine analogs and related C2-symmetric organocatalysts Full article
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Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539 |
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| Output data | Year: 2017, Volume: 15, Number: 33, Pages: 7028-7033 Pages count : 6 DOI: 10.1039/c7ob01852e | ||
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Abstract:
A simple and efficient synthesis of enantiomerically pure (1S,2S)-1,2-di(pyridin-2-yl)- and (1R,2R)-1,2-di(pyridin-4-yl)-ethane-1,2-diamines from commercial picolinaldehyde or isonicotinaldehyde and 2,2′-((1S,2S)-1,2-diaminoethane-1,2-diyl)diphenol (HPEN) via a stereospecific diaza-Cope rearrangement has been developed. Diamine (R,R)-2b was readily converted to novel diastereomeric ionic group-supported bis-prolinamides (R,S)-1b and (R,R)-1b which appeared to be efficient organocatalysts of asymmetric cross-aldol reactions in aldehyde/aldehyde, ketone/ketone or ketone/aldehyde reagent systems under neat conditions to afford corresponding aldols in high yields and with up to 99% ee. Furthermore, catalyst (R,S)-1b could be reused over 15 times in the same or similar catalytic reactions exhibiting close to original activity and a high level of stereoinduction.
Cite:
Kucherenko A.S.
, Kostenko A.A.
, Gerasimchuk V.V.
, Zlotin S.G.
Stereospecific diaza-Cope rearrangement as an efficient tool for the synthesis of DPEDA pyridine analogs and related C2-symmetric organocatalysts
Organic & Biomolecular Chemistry. 2017. V.15. N33. P.7028-7033. DOI: 10.1039/c7ob01852e WOS Scopus OpenAlex
Stereospecific diaza-Cope rearrangement as an efficient tool for the synthesis of DPEDA pyridine analogs and related C2-symmetric organocatalysts
Organic & Biomolecular Chemistry. 2017. V.15. N33. P.7028-7033. DOI: 10.1039/c7ob01852e WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000411448200021 |
| Scopus: | 2-s2.0-85028326189 |
| OpenAlex: | W2741201572 |