手性磷酸催化无环烯氨基甲酸酯与原位生成的邻醌甲基化物的对映选择性环化反应。
Chiral phosphoric acid catalyzed enantioselective annulation of acyclic enecarbamates to in situ-generated ortho-quinone methides.
作者信息
Gharui Chandan, Singh Shreya, Pan Subhas Chandra
机构信息
Department of Chemistry, Indian Institute of Technology Guwahati, 781039, India.
出版信息
Org Biomol Chem. 2017 Sep 13;15(35):7272-7276. doi: 10.1039/c7ob01766a.
PMID:28858366
Abstract
The first organocatalytic asymmetric reaction of acyclic enecarbamates with o-quinone methides is disclosed. BINOL-based phosphoric acid catalysts were found to be suitable for the annulation reaction. With 10 mol% of the TRIP catalyst, high yields as well as excellent diastereo- and enantioselectivities are achieved for a variety of 2,3,4-trisubstituted chroman products.
摘要
首次公开了无环烯氨基甲酸酯与邻醌甲基化物的有机催化不对称反应。发现基于联萘酚的磷酸催化剂适用于环化反应。使用10 mol%的TRIP催化剂，可实现多种2,3,4-三取代色满产物的高产率以及优异的非对映选择性和对映选择性。
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