Authors
Chandra Kanta De, Fabio Pesciaioli, Benjamin List
Publication date
2013/8/26
Journal
Angewandte Chemie
Volume
125
Issue
35
Description
The [3, 3]-diaza Cope rearrangement is a powerful synthetic principle that can be utilized to generate a CÀC bond at the expense of an NÀN bond. It forms the basis of important and fundamental acid-catalyzed transformations such as the Fischer indolization and the benzidine rearrangement (Scheme 1).[1–3] Recently, our group has established the first catalytic asymmetric variant of the Fischer indolization.[4] Two years ago, in light of the mechanistic similarities between the two reactions, we set up a program towards developing an asymmetric benzidine rearrangement. Such a transformation may find utility in the synthesis of highly useful chiral biaryls such as 1, 1’-binaphthyl-2, 2’-diamine (BINAM). Herein we report the successful realization of this idea with a benzidine rearrangement of N, N’-dinaphthylhydrazines catalyzed by a chiral phosphoric acid, furnishing the corresponding BINAM derivatives with high …
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