Enantio- and Diastereoselective Carbonyl-Ene Cyclization–Acetalization Tandem Reaction Catalyzed by Tris(pentafluorophenyl)borane-Assisted Chiral Phosphoric Acids
Abstract
Highly enantio- and diastereoselective carbonyl-ene cyclization was developed with the use of chiral Lewis acid-assisted chiral Brønsted acid (LBA) catalysts, which were prepared in situ from both sterically demanding tris(pentafluorophenyl)borane and chiral phosphoric acids. Along with the performance of standard carbonyl-ene cyclizations, carbonyl-ene cyclization–acetalization tandem reactions with the use of additional aldehydes were demonstrated with high enantio- and diastereoselectivities. On the basis of mechanistic examinations, a stepwise reaction pathway via tertiary carbocation intermediates involving possible transition states is proposed.
Journal
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- ACS Catalysis
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ACS Catalysis 11 (10), 6121-6127, 2021-05-21
ACS Publications
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Details 詳細情報について
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- CRID
- 1050571859101275264
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- NII Article ID
- 120007175364
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- ISSN
- 21555435
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- HANDLE
- 2237/0002001702
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- Text Lang
- en
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- Article Type
- journal article
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- Data Source
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- IRDB
- CiNii Articles