Superacid-Promoted Reactions of <i>N</i>-Acyliminium Ions: An Effective Route to Substituted 3-Oxo-1,2,3,4-tetrahydroisoquinolines and Related Products
作者:Douglas Klumpp、Yiliang Zhang、Patrick Kindelin、Daniel DeSchepper、Chong Zheng
DOI:10.1055/s-2006-942387
日期:2006.6
Intramolecular cyclizations involving N-acyliminium ions are shown to give products in good yields from reactions with CF3SO3H (triflic acid). The resulting 3-oxo-1,2,3,4-tetrahydroisoquinolines have been converted in high yields to 1,2-diaryl-1,2,3,4-tetrahydroisoquinolines, which have been recently shown to be selective estrogen receptor modulators. In a reaction using a chiral N-acyliminium ion, cyclization is found to occur in moderately high diastereoselectivity. Several examples of intermolecular triflic acid-promoted reactions are also reported.
研究显示,使用三氟甲磺酸(CF3SO3H)进行的N-酰基亚胺离子分子内环化反应能够以良好的收率得到产物。所得到的3-氧代-1,2,3,4-四氢异喹啉可以高收率地转化为1,2-二芳基-1,2,3,4-四氢异喹啉,这些化合物最近被证实是选择性雌激素受体调节剂。在使用手性N-酰基亚胺离子的反应中,发现环化反应具有中等程度的非对映选择性。研究还报道了几个三氟甲磺酸促进的分子间反应的例子。