A one-pot stereoselective synthesis of trans-1-aryl-2-aminotetralins from 2-arylethyl styrenes
摘要:
An efficient stereoselective synthesis of trans-1-aryl-2-aminotetralins has been achieved via Cu(OTf)(2) catalyzed one-pot aziridination and regioselective intramolecular arylation of in situ generated aziridines from 2-arylethyl styrenes and PhINSO(2)(4-NO(2)C(6)H(4)) [PhINNs]. Reaction of a mixture of E/Z-styrenes (<= 85:15) provided trans-N-protected-1-aryl-2-aminotetralins with high diastereoselectivity (dr > 95:5), which are important synthons for many artificial pharmaceuticals. (C) 2008 Elsevier Ltd. All rights reserved.
Isomerization During Olefin Metathesis: An Assessment of Potential Catalyst Culprits
作者:Carolyn S. Higman、Lucie Plais、Deryn E. Fogg
DOI:10.1002/cctc.201300886
日期:2013.12
Two ruthenium hydride complexes commonly proposed as agents of unintended isomerization during olefin metathesis are examined for their activity in isomerization of estragole, a representative allylbenzene. Neither proves kinetically competent to account for the levels of isomerization observed during cross‐metathesis of estragole by the second‐generation Grubbs catalyst. A structure–activity analysis
A Catalytic and Enantioselective Synthesis of<i>trans-</i>2-Amino-1- aryltetralins
作者:Saumen Hajra、Biswajit Maji、Dipakranjan Mal
DOI:10.1002/adsc.200800603
日期:2009.4
Abstractmagnified imageThe bis‐oxazoline‐copper complex‐catalyzed aziridination of alkenes followed by an intramolecular Friedel–Crafts alkylation of the tethered andin situgenerated aziridine provides a one‐pot, general and efficient method for the synthesis oftrans‐2‐amino‐1‐aryltetralins from a mixture of 2‐ arylethylstyrenes (E/Z≤85:15) with excellent dia‐ stereo‐ (dr>99:1) and enantioselectivities (up to 92%ee).