TY - JOUR
T1 - Gold(I)-Catalyzed Highly Diastereo- and Enantioselective Cyclization–[4+3] Annulation Cascades between 2-(1-Alkynyl)-2-alken-1-ones and Anthranils
AU - Kardile, Rahul Dadabhau
AU - Chao, Tzu Hsuan
AU - Cheng, Mu Jeng
AU - Liu, Rai Shung
N1 - Funding Information:
We thank the Ministry of Education (MOE 106N506CE1) and the Ministry of Science and Technology (MOST 107‐3017‐F‐007‐002), Taiwan, for financial support of this work.
Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2020/6/22
Y1 - 2020/6/22
N2 - This work reports gold-catalyzed [4+3]-annulations of 2-(1-alkynyl)-2-alken-1-ones with anthranils to yield epoxybenzoazepine products with excellent exo-diastereoselectivity (dr>25:1). The utility of this new gold catalysis is manifested by applicable substrates over a broad scope. More importantly, the enantioselective versions of these [4+3]-cycloadditions have been developed satisfactorily with chiral gold catalysts under ambient conditions (DCM, 0 °C); the ee levels range from 88.0–99.9 %. With DFT calculations, we postulate a stepwise pathway to rationalize the preferable exo-stereoselection.
AB - This work reports gold-catalyzed [4+3]-annulations of 2-(1-alkynyl)-2-alken-1-ones with anthranils to yield epoxybenzoazepine products with excellent exo-diastereoselectivity (dr>25:1). The utility of this new gold catalysis is manifested by applicable substrates over a broad scope. More importantly, the enantioselective versions of these [4+3]-cycloadditions have been developed satisfactorily with chiral gold catalysts under ambient conditions (DCM, 0 °C); the ee levels range from 88.0–99.9 %. With DFT calculations, we postulate a stepwise pathway to rationalize the preferable exo-stereoselection.
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U2 - 10.1002/anie.202001854
DO - 10.1002/anie.202001854
M3 - Article
C2 - 32212225
AN - SCOPUS:85083791956
SN - 1433-7851
VL - 59
SP - 10396
EP - 10400
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 26
ER -