The effective and unprecedented chiral BINOL phosphoric acid catalyzed (1–10 mol%) dearomatization of indoles through electrophilic activation of allenamides (ee up to 94%), is documented. Besides the synthesis of 3,3-disub- stituted indolenine cores, a dearomatization/hydrogen transfer cascade sequence is also presented as a new synthetic shortcut toward highly enantiomerically enriched indolines
Ciro Romano, Minqiang Jia, Magda Monari, Elisabetta Manoni, Marco Bandini (2014). Metal-Free Enantioselective Electrophilic Activation of Allenamides: Stereoselective Dearomatization of Indoles. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 53(50), 13854-13857 [10.1002/anie.201407518].
Metal-Free Enantioselective Electrophilic Activation of Allenamides: Stereoselective Dearomatization of Indoles
ROMANO, CIRO;JIA, MINQIANG;MONARI, MAGDA;MANONI, ELISABETTA;BANDINI, MARCO
2014
Abstract
The effective and unprecedented chiral BINOL phosphoric acid catalyzed (1–10 mol%) dearomatization of indoles through electrophilic activation of allenamides (ee up to 94%), is documented. Besides the synthesis of 3,3-disub- stituted indolenine cores, a dearomatization/hydrogen transfer cascade sequence is also presented as a new synthetic shortcut toward highly enantiomerically enriched indolinesI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
