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Asymmetric Synthesis and Application of Chiral Spirosilabiindanes
Author(s) -
Chang Xin,
Ma PeiLong,
Chen HongChao,
Li ChuanYing,
Wang Peng
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202002289
Subject(s) - enantiopure drug , phosphoramidite , chemistry , enantioselective synthesis , catalysis , intramolecular force , denticity , combinatorial chemistry , asymmetric hydrogenation , stereochemistry , organic chemistry , crystal structure , oligonucleotide , dna , biochemistry
Reported here is the development of a class of chiral spirosilabiindane scaffolds by Rh‐catalyzed asymmetric double hydrosilation, for the first time. Enantiopure SPSiOL (spirosilabiindane diol), a new type of chiral building block for the preparation of various chiral ligands and catalysts, was readily prepared on greater than 10 gram scale using this protocol. The potential of this new spirosilabiindane scaffold in asymmetric catalysis was preliminarily demonstrated by development of the corresponding monodentate phosphoramidite ligands (SPSiPhos), which were used in both a Rh‐catalyzed hydrogenation and a Pd‐catalyzed intramolecular carboamination.