Enantio- and Diastereoselective Betti/aza-Michael Sequence: Single Operated Preparation of Chiral 1,3-Disubstituted Isoindolines

Enantio- and Diastereoselective Betti/aza-Michael Sequence: Single Operated Preparation of Chiral 1,3-Disubstituted Isoindolines

The first enantio- and diastereoselective Betti/intramolecular aza-Michael sequence carried out using a C 3-symmetric chiral trisimidazoline organocatalyst is reported. The reaction of phenols and N-tosylimines bearing a Michael acceptor moiety afforded densely functionalized 1,3-disubstituted isoin...

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Veröffentlicht in:Organic letters 2017-10, Vol.19 (19), p.5426-5429
Hauptverfasser: Takizawa, Shinobu, Sako, Makoto, Abozeid, Mohamed Ahmed, Kishi, Kenta, Wathsala, H. D. P, Hirata, Shuichi, Murai, Kenichi, Fujioka, Hiromichi, Sasai, Hiroaki
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container_end_page 5429
container_issue 19
container_start_page 5426
container_title Organic letters
container_volume 19
creator Takizawa, Shinobu
Sako, Makoto
Abozeid, Mohamed Ahmed
Kishi, Kenta
Wathsala, H. D. P
Hirata, Shuichi
Murai, Kenichi
Fujioka, Hiromichi
Sasai, Hiroaki
description The first enantio- and diastereoselective Betti/intramolecular aza-Michael sequence carried out using a C 3-symmetric chiral trisimidazoline organocatalyst is reported. The reaction of phenols and N-tosylimines bearing a Michael acceptor moiety afforded densely functionalized 1,3-disubstituted isoindolines bearing two stereogenic centers as single diastereomers in high yields (≤93%) and excellent enantioselectivities (≤99.9%).
doi_str_mv 10.1021/acs.orglett.7b02693
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title Enantio- and Diastereoselective Betti/aza-Michael Sequence: Single Operated Preparation of Chiral 1,3-Disubstituted Isoindolines
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