Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12 Nishi-6, Kita-ku, Sapporo, 060-0812, Japan.
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan.
Chem Asian J. 2018 Sep 4;13(17):2378-2381. doi: 10.1002/asia.201800341. Epub 2018 May 9.
1,1'-Spirobiindane-7,7'-disulfonic acid (SPISA) and 1,1'-spirobiindane-7,7'-disulfonimide were synthesized from 1,1'-spirobiindane-7,7'-diol (SPINOL) in 4 steps using a Pd-catalyzed Newman-Kwart rearrangement as a key step. These new catalysts possessing a rigid spirocyclic backbone were evaluated in a catalytic asymmetric aminalization reaction, and SPISA/iPr NEt exhibited high enantioselectivity, demonstrating the utility of SPISA as a chiral Brønsted acid catalyst.
1,1'-螺双茚满-7,7'-二磺酸（SPISA）和 1,1'-螺双茚满-7,7'-二磺酰亚胺由 1,1'-螺双茚满-7,7'-二醇（SPINOL）经 4 步反应合成，其中钯催化的 Newmann-Kwart 重排为关键步骤。这些具有刚性螺环骨架的新型催化剂在催化不对称亚胺化反应中进行了评估，SPISA/iPr NEt 表现出高对映选择性，证明了 SPISA 作为手性布朗斯台德酸催化剂的实用性。
