9003-42-3Relevant articles and documents
Mechanistic Studies of the TRIP-Catalyzed Allylation with Organozinc Reagents
Hartmann, Peter E.,Lazzarotto, Mattia,Pletz, Jakob,Tanda, Stefan,Neu, Philipp,Goessler, Walter,Kroutil, Wolfgang,Boese, A. Daniel,Fuchs, Michael
, p. 9672 - 9679 (2020/09/03)
3,3-Bis(2,4,6-triisopropylphenyl)-1,1-binaphthyl-2,2-diyl hydrogenphosphate (TRIP) catalyzes the asymmetric allylation of aldehydes with organozinc compounds, leading to highly valuable structural motifs, like precursors to lignan natural products. Our previously reported mechanistic proposal relies on two reaction intermediates and requires further investigation to really understand the mode of action and the origins of stereoselectivity. Detailed ab initio calculations, supported by experimental data, render a substantially different mode of action to the allyl boronate congener. Instead of a Br?nsted acid-based catalytic activation, the chiral phosphate acts as a counterion for the Lewis acidic zinc ion, which provides the activation of the aldehyde.
Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes
Song, Shengjin,Lu, Ping,Liu, Huan,Cai, Sai-Hu,Feng, Chao,Loh, Teck-Peng
supporting information, p. 2869 - 2872 (2017/06/13)
A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.
Rhodium(iii)-catalyzed C-H allylation of electron-deficient alkenes with allyl acetates
Feng, Chao,Feng, Daming,Loh, Teck-Peng
supporting information, p. 342 - 345 (2015/01/09)
Rhodium-catalyzed C-H allylation of acrylamides with allyl acetates is reported. The use of weakly coordinating directing group resulted in high reaction efficiency, broad functionality tolerance and excellent γ-selectivity, which opens a new synthetic pathway for the access of 1,4-diene skeletons.
