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Divergent Asymmetric Reactions of ortho ‐Quinone Methides with α‐Thiocyanato Indanones for the Synthesis of Spiro‐ and Fused‐Indanones
Author(s) -
Liu Xianghui,
Wang Kai,
Liu Yan,
Li Can
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003647
Subject(s) - annulation , enantioselective synthesis , chemistry , combinatorial chemistry , cascade , solvent , reaction conditions , catalysis , base (topology) , hydrogen bond , organic chemistry , molecule , mathematics , mathematical analysis , chromatography
Reported in this work is a water triggered chemo‐divergent enantioselective spiro‐annulation and cascade reaction of ortho ‐quinone methides ( o ‐QMs) with α‐thiocyanato indanones catalyzed by a chiral organic base. In the case of spiro‐annulation, the use of trace amount of water as additive is critical to achieve high enantioselectivity (up to 96 % ee ). We found that a cascade reaction was enabled by just tuning the ratio of water in solvent. Accordingly, two new highly efficient asymmetric reactions for the divergent synthesis of spiro‐ and fused‐indanone scaffolds with excellent enantioselectivities (up to 99 % ee ) were developed. Mechanistic investigations suggest that interfacial hydrogen bonding may play an important role in achieving the switchable reaction pathways.