Premium
Synthesis of 1,1′‐Spirobiindane‐7,7′‐Disulfonic Acid and Disulfonimide: Application for Catalytic Asymmetric Aminalization
Author(s) -
Kurihara Takumaru,
Satake Shun,
Hatano Manabu,
Ishihara Kazuaki,
Yoshino Tatsuhiko,
Matsunaga Shigeki
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201800341
Subject(s) - catalysis , brønsted–lowry acid–base theory , enantioselective synthesis , chemistry , diol , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry
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/ i Pr 2 NEt exhibited high enantioselectivity, demonstrating the utility of SPISA as a chiral Brønsted acid catalyst.