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Spiro Compounds. Группа авторов
Читать онлайн.Название Spiro Compounds
Год выпуска 0
isbn 9781119567653
Автор произведения Группа авторов
Жанр Химия
Издательство John Wiley & Sons Limited
In other example of Bronsted acid catalysis, Tan and coworkers developed an enantioselective strategy for the construction of axially chiral compounds 277 (Scheme 3.25) [37]. This important class of spirocompounds is widely found in materials, organocatalysts, and ligands. The enantioselective intramolecular cyclization of ketals 278 to afford the SPINOL derivatives 277 is successfully catalyzed by the chiral phosphoric acid 279. Various ketals with different substitution patterns, including electron‐donating and electron‐withdrawing groups at the aryl ring, performed smoothly, affording the corresponding products 281–284 in high enantioselectivities and good to excellent yields (90−96% ee, 62−95% yield, conditions a). In the case of ketals bearing aromatic groups at the ortho position, the catalyst 280 (conditions b) was necessary to obtain the corresponding products. Remarkably, the catalytic system can be used at gram‐scale and the catalyst loading can be decreased as little as 0.1 mol%, despite higher temperature and prolonged reaction time are necessary.
Scheme 3.24 Organocatalytic asymmetric tandem Nazarov cyclization/semipinacol rearrangement.
Source: Modified from Yang et al. [36].
On the basis of mechanistic experiments, the authors propose that the reaction may initially form the intermediate 289, in situ generated from 288, which further proceed through the active o‐QM intermediate 290 to deliver the SPINOL derivative. The excellent stereocontrol was attributed to the simultaneous interaction between the bifunctional phosphoric acid and intermediate 291 via hydrogen‐bonding interactions.
Scheme 3.25 Chiral phosphoric acid‐catalyzed asymmetric synthesis of SPINOL derivatives.
Source: Modified from Li et al. [37].
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